Penamecillin

Penamecillin
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	J01CE06 (WHO) ;
Identifiers
	IUPAC name (acetyloxy)methyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;
CAS Number	983-85-7 ;
PubChem CID	13795;
ChemSpider	8426255 ;
UNII	H0P1YE5581;
KEGG	D05406 ;
ChEBI	CHEBI:131733 ;
CompTox Dashboard (EPA)	DTXSID10243547 ;
ECHA InfoCard	100.012.338
Chemical and physical data
Formula	C19H22N2O6S
Molar mass	406.45 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)OCOC(=O)[C@H]1C(S[C@H]2N1C(=O)[C@H]2NC(=O)CC3=CC=CC=C3)(C)C;
	InChI InChI=1S/C19H22N2O6S/c1-11(22)26-10-27-18(25)15-19(2,3)28-17-14(16(24)21(15)17)20-13(23)9-12-7-5-4-6-8-12/h4-8,14-15,17H,9-10H2,1-3H3,(H,20,23)/t14-,15+,17-/m1/s1 ; Key:NLOOMWLTUVBWAW-HLLBOEOZSA-N ;
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Penamecillin, an acetoxymethyl ester of benzylpenicillin, is a prodrug processed to benzylpenicillin by esterases.^[1] It has no detectable teratogenic risk to the fetus.^[2]

References

^ Agersborg HP, Batchelor A, Cambridge GW, Rule AW (March 1966). "The pharmacology of penamecillin". British Journal of Pharmacology and Chemotherapy. 26 (3): 649–655. doi:10.1111/j.1476-5381.1966.tb01844.x. PMC 1510697. PMID 4959939.
^ Czeizel AE, Rockenbauer M, Sørensen HT, Olsen J (1999). "The Safety of Penicillin V: Oral Penamecillin Use During Pregnancy The Importance and Limitation of Recall Bias". Congenital Anomalies. 39 (4): 267–279. doi:10.1111/j.1741-4520.1999.tb00566.x. ISSN 0914-3505.

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[1] Agersborg HP, Batchelor A, Cambridge GW, Rule AW (March 1966). "The pharmacology of penamecillin". British Journal of Pharmacology and Chemotherapy. 26 (3): 649–655. doi:10.1111/j.1476-5381.1966.tb01844.x. PMC 1510697. PMID 4959939.

[2] Czeizel AE, Rockenbauer M, Sørensen HT, Olsen J (1999). "The Safety of Penicillin V: Oral Penamecillin Use During Pregnancy The Importance and Limitation of Recall Bias". Congenital Anomalies. 39 (4): 267–279. doi:10.1111/j.1741-4520.1999.tb00566.x. ISSN 0914-3505.

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