Prazocillin

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H18Cl2N4O4S
Molecular Weight	469.342
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(N(N=C1)C2=C(Cl)C=CC=C2Cl)C(=O)N[C@H]3[C@H]4SC(C)(C)[C@@H](N4C3=O)C(O)=O

InChI

InChIKey=XRCKXULNIUSXFZ-HYSWKAIVSA-N

InChI=1S/C19H18Cl2N4O4S/c1-8-7-22-25(13-9(20)5-4-6-10(13)21)12(8)15(26)23-11-16(27)24-14(18(28)29)19(2,3)30-17(11)24/h4-7,11,14,17H,1-3H3,(H,23,26)(H,28,29)/t11-,14+,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C19H18Cl2N4O4S
Molecular Weight	469.342
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5142734 | https://www.ncbi.nlm.nih.gov/pubmed/5004081 | https://www.ncbi.nlm.nih.gov/pubmed/4992224

Prazocillin is 6-aminopenicillanic acid derivative patented by Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt. as a bactericidal compound. The activity of Prazocillin against Staphylococcus aureus strains was the same as that of dikloxacillin, but Prazocillin was more active against Bacillus subtilis ATCC 6633. Prazocillin had a bactericidal effect on a penicillin-resistant S. aureus strain at concentrations of 1 μg/ml. Pyrazocillin inhibits bacterial penicillinase in vitro.

Originator

Approval Year

PubMed

Title	Date	PubMed
[Clinico-pharmacological test of a new penicillinase-stable penicillin, pyrazocillin, F 75 ].	1971	5142734

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:01:09 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:09 GMT 2025`
Record UNII	IRZ1462XXF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Prazocillin

Official Name

English

1-(2,6-Dichlorophenyl)-4-methyl-5-pyrazolyl penicillin

Preferred Name

English

(2S,5R,6R)-6-[[[1-(2,6-Dichlorophenyl)-4-methyl-1H-pyrazol-5-yl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Systematic Name

English

Pyrazocillin

Common Name

English

prazocillin [INN]

Common Name

English

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[[1-(2,6-dichlorophenyl)-4-methyl-1H-pyrazol-5-yl]carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1500