Drotaverine

Drotaverine (INN, also known as drotaverin) is an antispasmodic drug, used to enhance cervical dilation during childbirth.[2]^:283

Drotaverine

Clinical data
Trade names	No-Spa, Doverin
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, intravenous, intramuscular
ATC code	A03AD02 (WHO)
Legal status
Legal status	OTC (tablets), ℞-only (solution for injection) (RU)[1]
Pharmacokinetic data
Bioavailability	Highly variable (~65%), peak at 45–60 min
Protein binding	95–98%
Metabolism	Hepatic
Elimination half-life	7–16 hours
Excretion	>50% in urine and ~30% in bile[1]
Identifiers
IUPAC name (Z)-1-(3,4-diethoxybenzylidene)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline
CAS Number	14009-24-6
PubChem CID	1712095
DrugBank	DB06751
ChemSpider	1361582
UNII	98QS4N58TW
KEGG	D07879
ChEMBL	ChEMBL551978
CompTox Dashboard (EPA)	DTXSID60161227
ECHA InfoCard	100.110.916
Chemical and physical data
Formula	C24H31NO4
Molar mass	397.515 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O(c1ccc(cc1OCC)\C=C3\c2c(cc(OCC)c(OCC)c2)CCN3)CC
InChI InChI=1S/C24H31NO4/c1-5-26-21-10-9-17(14-22(21)27-6-2)13-20-19-16-24(29-8-4)23(28-7-3)15-18(19)11-12-25-20/h9-10,13-16,25H,5-8,11-12H2,1-4H3/b20-13- Key:OMFNSKIUKYOYRG-MOSHPQCFSA-N
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It is structurally related to papaverine, is a selective inhibitor of phosphodiesterase 4, and has no anticholinergic effects.[3]

It is available in Asian and Central and Eastern European countries under several brand names.[4]

An article from 2013 described the effects from overdose (in a 19-year-old woman) as including vomiting, seizures and fatal cardiac toxicity.[5]

In 2016, the young Russian chess player Ivan Bukavshin died of a massive overdose (or poisoning) of the drug, which was originally thought to be a stroke.[6] his doses was 17 mg/kg in the blood stream.

Counterfeits

In Israel the product is known under the brand name "No-Spa" by the general public[7] which did not receive a permit to be distributed by the health ministry,[8] However due to high demand local medical counterfeiters had managed to smuggle No-Spa tablets during the years.[8]

In 2008 the Israeli health organization warned consumers from counterfeit No-SPA pills after a smuggler had been arrested at the Ben Gurion Airport with several thousand pills.[9][10]

In 2011 Israeli patent and trade mark office declined the use of the No-SPA.[7]

References

1. "Инструкция по применению препарата Но-шпа // No-Spa (tablets) Full Prescribing Information". National Register of Drugs (in Russian). Chinoin Pharmaceutical and Chemical Works. pp. 3–8.
2. Padubidri V and Anand E. Title Textbook of Obstetrics. BI Publications Pvt Ltd, 2006 ISBN 9788172252236
3. "The DrugBank database: Drotaverine". DrugBank Version 4.1. The Metabolomics Innovation Centre. Retrieved 9 August 2014.
4. Drotaverine - Drugs.com Drugs.com international listings for drotaverine Page accessed June 28, 2015
5. Drotaverine overdose (case report) Reactions Weekly, Volume 1481 (1), page 17.
6. Silence, lack of will, indifference (Russian, Chess-News)
7. NO-SPA (also pronounced as No-SHPA) trade mark registration decision 202248, Israeli patent and trade mark office,11 July 2007
8. Health Ministry: Fake drug had been smuggled NRG, 11 March 2009
9. Health Ministry: Counterfeit NO-SPA pills had been smuggled and are considered a health risk, Globes
10. "משרד הבריאות מזהיר משימוש בתרופה לא מאושרת בשם: No-Spa".