Testosterone cypionate

Testosterone cypionate, sold under the brand name Depo-Testosterone among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men.[2][3][4] It is also used in hormone therapy for transgender men.[5] It is given by injection into muscle or subcutaneously, once every one to four weeks, depending on clinical indication.[4][6][7][8]

Testosterone cypionate

Clinical data
Trade names	Depo-Testosterone, others
Other names	TC; TCPP; Testosterone cipionate; Testosterone cyclopentylpropionate; Testosterone cyclopentanepropionate; Testosterone 17β-cyclopentylpropionate
Routes of administration	Intramuscular injection
Drug class	Androgen; Anabolic steroid; Androgen ester
Legal status
Legal status	CA: Schedule IV US: Schedule III
Pharmacokinetic data
Bioavailability	Oral: very low Intramuscular: very high
Metabolism	Liver
Elimination half-life	~8 days i.m.)[1]
Excretion	90% Urine; 6% feces[1]
Identifiers
IUPAC name [(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] 3-cyclopentylpropanoate
CAS Number	58-20-8
PubChem CID	441404
DrugBank	DB13943
ChemSpider	390140
UNII	M0XW1UBI14
KEGG	D00957
ChEMBL	ChEMBL1201101
ECHA InfoCard	100.000.335
Chemical and physical data
Formula	C27H40O3
Molar mass	412.614 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCC4CCCC4)CCC5=CC(=O)CC[C@]35C
InChI InChI=1S/C27H40O3/c1-26-15-13-20(28)17-19(26)8-9-21-22-10-11-24(27(22,2)16-14-23(21)26)30-25(29)12-7-18-5-3-4-6-18/h17-18,21-24H,3-16H2,1-2H3/t21-,22-,23-,24-,26-,27-/m0/s1 Key:HPFVBGJFAYZEBE-ZLQWOROUSA-N

Side effects of testosterone cypionate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[4] The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT).[9][4] It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization and suitable for androgen replacement therapy.[4] Testosterone cypionate is a testosterone ester and a long-lasting prodrug of testosterone in the body.[6][2][3] Because of this, it is considered to be a natural and bioidentical form of testosterone.[10]

Testosterone cypionate was introduced for medical use in 1951.[11][12] Along with testosterone enanthate, testosterone undecanoate, and testosterone propionate, it is one of the most commonly used testosterone esters.[9][4] It is used mainly in the United States.[4] In addition to its medical use, testosterone cypionate is used to improve physique and performance.[4] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[4]

Medical uses

See also: Androgen replacement therapy § Medical uses, and Anabolic steroid § Medical

Testosterone cypionate is used primarily in androgen replacement therapy.[13] It is currently FDA approved for the treatment of primary or hypogonadotropic hypogonadism (either congenital or acquired). Its safety in andropause (late-onset hypogonadism in men) has not yet been established.[1] It is currently used off-label for breast cancer, breast disorders, delayed puberty in boys, oligospermia (low sperm count), hormone replacement therapy in transgender men,[8] and osteoporosis.[14][1]

Androgen replacement therapy formulations and dosages used in men

Route	Medication	Major brand names	Form	Dosage
Oral	Testosterone^a	–	Tablet	400–800 mg/day (in divided doses)
	Testosterone undecanoate	Andriol, Jatenzo	Capsule	40–80 mg/2–4x day (with meals)
	Methyltestosterone^b	Android, Metandren, Testred	Tablet	10–50 mg/day
	Fluoxymesterone^b	Halotestin, Ora-Testryl, Ultandren	Tablet	5–20 mg/day
	Metandienone^b	Dianabol	Tablet	5–15 mg/day
	Mesterolone^b	Proviron	Tablet	25–150 mg/day
Buccal	Testosterone	Striant	Tablet	30 mg 2x/day
	Methyltestosterone^b	Metandren, Oreton Methyl	Tablet	5–25 mg/day
Sublingual	Testosterone^b	Testoral	Tablet	5–10 mg 1–4x/day
	Methyltestosterone^b	Metandren, Oreton Methyl	Tablet	10–30 mg/day
Intranasal	Testosterone	Natesto	Nasal spray	11 mg 3x/day
Transdermal	Testosterone	AndroGel, Testim, TestoGel	Gel	25–125 mg/day
		Androderm, AndroPatch, TestoPatch	Non-scrotal patch	2.5–15 mg/day
		Testoderm	Scrotal patch	4–6 mg/day
		Axiron	Axillary solution	30–120 mg/day
	Androstanolone (DHT)	Andractim	Gel	100–250 mg/day
Rectal	Testosterone	Rektandron, Testosteron^b	Suppository	40 mg 2–3x/day
Injection (IM or SC)	Testosterone	Andronaq, Sterotate, Virosterone	Aqueous suspension	10–50 mg 2–3x/week
	Testosterone propionate^b	Testoviron	Oil solution	10–50 mg 2–3x/week
	Testosterone enanthate	Delatestryl	Oil solution	50–250 mg 1x/1–4 weeks
		Xyosted	Auto-injector	50–100 mg 1x/week
	Testosterone cypionate	Depo-Testosterone	Oil solution	50–250 mg 1x/1–4 weeks
	Testosterone isobutyrate	Agovirin Depot	Aqueous suspension	50–100 mg 1x/1–2 weeks
	Testosterone phenylacetate^b	Perandren, Androject	Oil solution	50–200 mg 1x/3–5 weeks
	Mixed testosterone esters	Sustanon 100, Sustanon 250	Oil solution	50–250 mg 1x/2–4 weeks
	Testosterone undecanoate	Aveed, Nebido	Oil solution	750–1,000 mg 1x/10–14 weeks
	Testosterone buciclate^a	–	Aqueous suspension	600–1,000 mg 1x/12–20 weeks
Implant	Testosterone	Testopel	Pellet	150–1,200 mg/3–6 months
Notes: Men produce about 3 to 11 mg testosterone per day (mean 7 mg/day in young men). Footnotes: ^a = Never marketed. ^b = No longer used and/or no longer marketed. Sources: See template.

Medications and dosages used in masculinizing hormone therapy for transgender men

Medication	Brand names	Type	Route	Dosage
Testosterone undecanoate	Andriol, Jatenzo	Androgen	Oral	40–80 mg/2–3x day (with meals)
Testosterone	Striant	Androgen	Buccal	30 mg 2x/day
	Natesto		Nasal spray	11 mg 3x/day
	AndroGel, others		Transdermal gel	25–100 mg/day
	Androderm, others		Transdermal patch	2.5–10 mg/day
	Axiron		Axillary solution	30–120 mg/day
	Testopel		Subcutaneous implant	150–600 mg/3–6 months
Testosterone enanthate	Delatestryl, others	Androgen	Injection (IM or SC)	50–100 mg/week or 100–250 mg/2–4 weeks
Testosterone cypionate	Depo-Testosterone, others	Androgen	Injection (IM or SC)	50–100 mg/week or 100–250 mg/2–4 weeks
Testosterone isobutyrate	Agovirin Depot	Androgen	Injection (IM or SC)	50–100 mg/week
Mixed testosterone esters	Sustanon 250, others	Androgen	Injection (IM or SC)	250 mg/2–3 weeks or 500 mg/3–6 weeks
Testosterone undecanoate	Aveed, Nebido, others	Androgen	Injection (IM or SC)	750–1,000 mg/10–14 weeks
GnRH analogue	Various	GnRH modulator	Parenteral (various)	Variable
Elagolix	Orilissa	GnRH antagonist	Oral	150 mg/day or 200 mg/twice a day
Medroxyprogesterone acetate^a	Provera, others	Progestin	Oral	5–10 mg/day
	Depo-Provera, others		Injection (IM)	150 mg/3 months
	Depo-SubQ Provera 104		Injection (SC)	104 mg/3 months
Lynestrenol^a	Orgametril, others	Progestin	Oral	5–10 mg/day
Finasteride^b	Propecia, Proscar	5α-Reductase inhibitor	Oral	1 mg/day
Dutasteride^b	Avodart	5α-Reductase inhibitor	Oral	0.5 mg/day
Notes: Testes produce 3 to 11 mg testosterone per day (mean 7 mg/day in young men). Footnotes: ^a = For suppression of menses. ^b = For prevention/treatment of scalp hair loss. Sources: See template.

Androgen replacement therapy formulations and dosages used in women

Route	Medication	Major brand names	Form	Dosage
Oral	Testosterone undecanoate	Andriol, Jatenzo	Capsule	40–80 mg 1x/1–2 days
	Methyltestosterone	Metandren, Estratest	Tablet	0.5–10 mg/day
	Fluoxymesterone	Halotestin	Tablet	1–2.5 mg 1x/1–2 days
	Normethandrone^a	Ginecoside	Tablet	5 mg/day
	Tibolone	Livial	Tablet	1.25–2.5 mg/day
	Prasterone (DHEA)^b	–	Tablet	10–100 mg/day
Sublingual	Methyltestosterone	Metandren	Tablet	0.25 mg/day
Transdermal	Testosterone	Intrinsa	Patch	150–300 μg/day
		AndroGel	Gel, cream	1–10 mg/day
Vaginal	Prasterone (DHEA)	Intrarosa	Insert	6.5 mg/day
Injection	Testosterone propionate^a	Testoviron	Oil solution	25 mg 1x/1–2 weeks
	Testosterone enanthate	Delatestryl, Primodian Depot	Oil solution	25–100 mg 1x/4–6 weeks
	Testosterone cypionate	Depo-Testosterone, Depo-Testadiol	Oil solution	25–100 mg 1x/4–6 weeks
	Testosterone isobutyrate^a	Femandren M, Folivirin	Aqueous suspension	25–50 mg 1x/4–6 weeks
	Mixed testosterone esters	Climacteron^a	Oil solution	150 mg 1x/4–8 weeks
		Omnadren, Sustanon	Oil solution	50–100 mg 1x/4–6 weeks
	Nandrolone decanoate	Deca-Durabolin	Oil solution	25–50 mg 1x/6–12 weeks
	Prasterone enanthate^a	Gynodian Depot	Oil solution	200 mg 1x/4–6 weeks
Implant	Testosterone	Testopel	Pellet	50–100 mg 1x/3–6 months
Notes: Premenopausal women produce about 230 ± 70 μg testosterone per day (6.4 ± 2.0 mg testosterone per 4 weeks), with a range of 130 to 330 μg per day (3.6–9.2 mg per 4 weeks). Footnotes: ^a = Mostly discontinued or unavailable. ^b = Over-the-counter. Sources: See template.

Androgen/anabolic steroid dosages for breast cancer

Route	Medication	Form	Dosage
Oral	Methyltestosterone	Tablet	30–200 mg/day
	Fluoxymesterone	Tablet	10–40 mg 3x/day
	Calusterone	Tablet	40–80 mg 4x/day
	Normethandrone	Tablet	40 mg/day
Buccal	Methyltestosterone	Tablet	25–100 mg/day
Injection (IM or SC)	Testosterone propionate	Oil solution	50–100 mg 3x/week
	Testosterone enanthate	Oil solution	200–400 mg 1x/2–4 weeks
	Testosterone cypionate	Oil solution	200–400 mg 1x/2–4 weeks
	Mixed testosterone esters	Oil solution	250 mg 1x/week
	Methandriol	Aqueous suspension	100 mg 3x/week
	Androstanolone (DHT)	Aqueous suspension	300 mg 3x/week
	Drostanolone propionate	Oil solution	100 mg 1–3x/week
	Metenolone enanthate	Oil solution	400 mg 3x/week
	Nandrolone decanoate	Oil solution	50–100 mg 1x/1–3 weeks
	Nandrolone phenylpropionate	Oil solution	50–100 mg/week
Note: Dosages are not necessarily equivalent. Sources: See template.

Side effects

See also: Anabolic steroid § Adverse effects, and Androgen replacement therapy § Adverse effects

Side effects of testosterone cypionate include virilization among others.[4]

Pharmacology

Pharmacodynamics

See also: Testosterone § Mechanism of action, and Anabolic steroid § Pharmacology

Androgenic vs. anabolic activity
of androgens/anabolic steroids

Medication	Ratio^a
Testosterone	~1:1
Androstanolone (DHT)	~1:1
Methyltestosterone	~1:1
Methandriol	~1:1
Fluoxymesterone	1:1–1:15
Metandienone	1:1–1:8
Drostanolone	1:3–1:4
Metenolone	1:2–1:30
Oxymetholone	1:2–1:9
Oxandrolone	1:3–1:13
Stanozolol	1:1–1:30
Nandrolone	1:3–1:16
Ethylestrenol	1:2–1:19
Norethandrolone	1:1–1:20
Notes: In rodents. Footnotes: ^a = Ratio of androgenic to anabolic activity. Sources: See template.

Testosterone cypionate is a prodrug of testosterone and is an androgen and anabolic–androgenic steroid (AAS). That is, it is an agonist of the androgen receptor (AR).

Pharmacokinetics

The pharmacokinetics of testosterone cypionate via depot intramuscular injection, including its elimination half-life and duration of action, are said to be extremely comparable to and hence essentially the same as those of testosterone enanthate.[4][3] As such, testosterone cypionate and testosterone enanthate are considered to be "functionally interchangeable" as medications.[4] For reference, testosterone enanthate has an elimination half-life of 4.5 days and a mean residence time of 8.5 days and requires frequent administration of approximately once per week.[15] Large fluctuations in testosterone levels result with it, with levels initially being elevated and supraphysiological.[15] The pharmacokinetics of testosterone cypionate have been studied and reported.[16]

Pharmacokinetics of testosterone esters

Testosterone ester	Form	Route	Tmax	t1/2	MRT
Testosterone undecanoate	Oil-filled capsules	Oral	?	1.6 hours	3.7 hours
Testosterone propionate	Oil solution	Intramuscular injection	?	0.8 days	1.5 days
Testosterone enanthate	Castor oil solution	Intramuscular injection	10 days	4.5 days	8.5 days
Testosterone undecanoate	Tea seed oil solution	Intramuscular injection	13.0 days	20.9 days	34.9 days
Testosterone undecanoate	Castor oil solution	Intramuscular injection	11.4 days	33.9 days	36.0 days
Testosterone buciclate^a	Aqueous suspension	Intramuscular injection	25.8 days	29.5 days	60.0 days
Notes: Testosterone cypionate has similar pharmacokinetics to TE. Footnotes: ^a = Never marketed. Sources: See template.

Parenteral durations of androgens/anabolic steroids

Medication	Form	Major brand names	Duration
Testosterone	Aqueous suspension	Andronaq, Sterotate, Virosterone	2–3 days
Testosterone propionate	Oil solution	Androteston, Perandren, Testoviron	3–4 days
Testosterone phenylpropionate	Oil solution	Testolent	8 days
Testosterone isobutyrate	Aqueous suspension	Agovirin Depot, Perandren M	14 days
Mixed testosterone esters^a	Oil solution	Triolandren	10–20 days
Mixed testosterone esters^b	Oil solution	Testosid Depot	14–20 days
Testosterone enanthate	Oil solution	Delatestryl	14–28 days
Testosterone cypionate	Oil solution	Depovirin	14–28 days
Mixed testosterone esters^c	Oil solution	Sustanon 250	28 days
Testosterone undecanoate	Oil solution	Aveed, Nebido	100 days
Testosterone buciclate^d	Aqueous suspension	20 Aet-1, CDB-1781^e	90–120 days
Nandrolone phenylpropionate	Oil solution	Durabolin	10 days
Nandrolone decanoate	Oil solution	Deca Durabolin	21–28 days
Methandriol	Aqueous suspension	Notandron, Protandren	8 days
Methandriol bisenanthoyl acetate	Oil solution	Notandron Depot	16 days
Metenolone acetate	Oil solution	Primobolan	3 days
Metenolone enanthate	Oil solution	Primobolan Depot	14 days
Note: All are via i.m. injection. Footnotes: ^a = TP, TV, and TUe. ^b = TP and TKL. ^c = TP, TPP, TiCa, and TD. ^d = Studied but never marketed. ^e = Developmental code names. Sources: See template.

Chemistry

See also: Androgen ester and List of androgen esters

Testosterone cypionate, or testosterone 17β-cyclopentylpropionate, is a synthetic androstane steroid and a derivative of testosterone.[17][18] It is an androgen ester; specifically, it is the C17β cyclopentylpropionate (cypionate) ester of testosterone.[17][18]

Structural properties of major testosterone esters

Androgen	Structure	Ester				Relative mol. weight	Relative T content^b	Duration^c
		Position	Moiety	Type	Length^a			Rank	Group
Testosterone		–	–	–	–	1.00	1.00	11	Short
Testosterone propionate		C17β	Propanoic acid	Straight-chain fatty acid	3	1.19	0.84	10	Short
Testosterone isobutyrate		C17β	Isobutyric acid	Aromatic fatty acid	– (~3)	1.24	0.80	9	Moderate
Testosterone cypionate		C17β	Cyclopentylpropanoic acid	Aromatic fatty acid	– (~6)	1.43	0.70	8	Moderate
Testosterone phenylpropionate		C17β	Phenylpropanoic acid	Aromatic fatty acid	– (~6)	1.46	0.69	7	Moderate
Testosterone isocaproate		C17β	Isohexanoic acid	Branched-chain fatty acid	– (~5)	1.34	0.75	6	Moderate
Testosterone caproate		C17β	Hexanoic acid	Straight-chain fatty acid	6	1.35	0.75	5	Moderate
Testosterone enanthate		C17β	Heptanoic acid	Straight-chain fatty acid	7	1.39	0.72	4	Moderate
Testosterone decanoate		C17β	Decanoic acid	Straight-chain fatty acid	10	1.53	0.65	3	Long
Testosterone undecanoate		C17β	Undecanoic acid	Straight-chain fatty acid	11	1.58	0.63	2	Long
Testosterone buciclate^d		C17β	Bucyclic acid^e	Aromatic carboxylic acid	– (~9)	1.58	0.63	1	Long
Footnotes: ^a = Length of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic fatty acids. ^b = Relative testosterone content by weight (i.e., relative androgenic/anabolic potency). ^c = Duration by intramuscular or subcutaneous injection in oil solution (except TiB and TB, which are in aqueous suspension). ^d = Never marketed. ^e = Bucyclic acid = trans-4-Butylcyclohexane-1-carboxylic acid. Sources: See individual articles.

History

Testosterone cypionate was first synthesized in 1951[19] and was introduced for medical use in the United States the same year under the brand name Depo-Testosterone.[11][12]

Society and culture

Generic names

Testosterone cypionate is the generic name of the drug and its USP.[17][18][20][21] The drug does not have an INN, USAN, or BAN.[17][18][20][21] It has also been referred to as testosterone cipionate, as well as testosterone cyclopentylpropionate or testosterone cyclopentanepropionate.[17][18][20][21]

Brand names

Testosterone cypionate is or has been marketed under a variety of brand names, including:[17][18][20][21]

• Andro Cyp
• Andronaq LA
• Andronate
• Dep Andro
• Dep Test
• Deposteron
• Depostomead
• Depotest
• Depo-Testosterone
• Depovirin
• Durandro
• Duratest
• Jectatest
• Malogen CYP
• Pertestis
• Testa-C
• Testadiate Depo
• Testex Elmu Prolongatum
• Testoject LA
• Virilon

Availability

See also: List of androgens/anabolic steroids available in the United States

Testosterone cypionate is marketed in the United States.[4][18] It is not widely available outside of the United States, though it has been marketed in Canada, Australia, Spain, Brazil, and South Africa.[4][18]

Legal status

Testosterone cypionate, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act and a schedule IV controlled substance in Canada under the Controlled Drugs and Substances Act.[22][23]

References

1. Pfizer. "Depo-Testosterone; testosterone cypionate injection, USP" (PDF). U.S. Food and Drug Administration.CS1 maint: uses authors parameter (link)
2. Nieschlag E, Behre HM, Nieschlag S (26 July 2012). Testosterone: Action, Deficiency, Substitution. Cambridge University Press. pp. 315–. ISBN 978-1-107-01290-5.
3. Nieschlag E, Behre HM, Nieschlag S (13 January 2010). Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. pp. 442–. ISBN 978-3-540-78355-8.
4. William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 212–216. ISBN 978-0-9828280-1-4.
5. Irwig MS (April 2017). "Testosterone therapy for transgender men". The Lancet. Diabetes & Endocrinology. 5 (4): 301–311. doi:10.1016/S2213-8587(16)00036-X. PMID 27084565.
6. Becker KL (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1185, 1187. ISBN 978-0-7817-1750-2.
7. Ayd FJ (2000). Lexicon of Psychiatry, Neurology, and the Neurosciences. Lippincott Williams & Wilkins. pp. 974–. ISBN 978-0-7817-2468-5.
8. Hembree WC, Cohen-Kettenis PT, Gooren L, Hannema SE, Meyer WJ, Murad MH, et al. (November 2017). "Endocrine Treatment of Gender-Dysphoric/Gender-Incongruent Persons: An Endocrine Society Clinical Practice Guideline". The Journal of Clinical Endocrinology and Metabolism. 102 (11): 3869–3903. doi:10.1210/jc.2017-01658. PMID 28945902.
9. Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
10. Santoro N, Braunstein GD, Butts CL, Martin KA, McDermott M, Pinkerton JV (April 2016). "Compounded Bioidentical Hormones in Endocrinology Practice: An Endocrine Society Scientific Statement". The Journal of Clinical Endocrinology and Metabolism. 101 (4): 1318–43. doi:10.1210/jc.2016-1271. PMID 27032319.
11. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 3170–. ISBN 978-0-8155-1856-3.
12. Hoberman J (21 February 2005). Testosterone Dreams: Rejuvenation, Aphrodisia, Doping. University of California Press. pp. 134–. ISBN 978-0-520-93978-3.
13. HRTGuru corp. "What is Testosterone Cypionate".CS1 maint: uses authors parameter (link)
14. "Testosterone cypionate drug profile". Adis Insight.
15. Payne AH, Hardy MP (28 October 2007). The Leydig Cell in Health and Disease. Springer Science & Business Media. pp. 423–. ISBN 978-1-59745-453-7.
16. Nankin HR (June 1987). "Hormone kinetics after intramuscular testosterone cypionate". Fertility and Sterility. 47 (6): 1004–9. doi:10.1016/S0015-0282(16)59237-1. PMID 3595893.
17. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 641–642. ISBN 978-1-4757-2085-3.
18. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1002–1004. ISBN 978-3-88763-075-1.
19. Dekansi J, Chapman RN (September 1953). "Testosterone phenyl propionate (TPP): biological trials with a new androgen". Br J Pharmacol Chemother. 8 (3): 271–7. doi:10.1111/j.1476-5381.1953.tb00793.x. PMC 1509286. PMID 13093945.
20. Morton I, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN 978-94-011-4439-1.
21. "Testosterone". Drugs.com International.
22. Karch SB (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.
23. Lilley LL, Snyder JS, Collins SR (5 August 2016). Pharmacology for Canadian Health Care Practice. Elsevier Health Sciences. pp. 50–. ISBN 978-1-77172-066-3.