Ethacridine lactate

Ethacridine lactate (ethacridine monolactate monohydrate, acrinol, trade name Rivanol) is an aromatic organic compound based on acridine. Its formal name is 2-ethoxy-6,9-diaminoacridine monolactate monohydrate. It forms orange-yellow crystals with a melting point of 226 °C and it has a stinging smell.

Ethacridine lactate

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	B05CA08 (WHO) D08AA01 (WHO)
Identifiers
IUPAC name 7-Ethoxyacridine-3,9-diamine 2-hydroxypropanoic acid
CAS Number	1837-57-6^N
PubChem CID	15789
ChemSpider	15012^Y
UNII	7T7T2I9823
KEGG	D01248^Y
ChEMBL	ChEMBL582355^Y
CompTox Dashboard (EPA)	DTXSID10872472
ECHA InfoCard	100.015.826
Chemical and physical data
Formula	C18H21N3O4
Molar mass	343.37 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=C(O)C(O)C.O(c2ccc1nc3c(c(c1c2)N)ccc(c3)N)CC
InChI InChI=1S/C15H15N3O.C3H6O3/c1-2-19-10-4-6-13-12(8-10)15(17)11-5-3-9(16)7-14(11)18-13;1-2(4)3(5)6/h3-8H,2,16H2,1H3,(H2,17,18);2,4H,1H3,(H,5,6)^Y Key:IYLLULUTZPKQBW-UHFFFAOYSA-N^Y
^NY (what is this?)  (verify)

Its primary use is as an antiseptic[1] in solutions of 0.1%. It is effective against mostly Gram-positive bacteria, such as Streptococci and Staphylococci, but ineffective against Gram-negative bacteria such as Pseudomonas aeruginosa.[2]

Ethacridine is also used as an agent for second trimester abortion. Up to 150 ml of a 0.1% solution is instilled extra-amniotically using a foley catheter. After 20 to 40 hours, 'mini labor' ensues. In China, an intra-amniotic method has also been used.[3] Ethacridine as an abortifacient is found to be safer and better tolerated than 20% hypertonic saline.

References

1. Merck Index, 11th Ed., 3668
2. Adarchenko AA, Krasil'nikov AP, Sobeshchuk OP (1989). "[Antiseptic sensitivity of clinical strains of Pseudomonas aeruginosa]". Antibiotiki I Khimioterapiia (in Russian). 34 (12): 902–7. PMID 2517004.
3. Tien, K. H. (1983). "Intraamniotic injection of ethacridine for second-trimester induction of labor". Obstetrics and Gynecology. 61 (6): 733–736. PMID 6843933.