ADICILLIN

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H21N3O6S
Molecular Weight	359.398
Optical Activity	( + / - )
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)CCC[C@@H](N)C(O)=O)C(=O)N2[C@H]1C(O)=O

InChI

InChIKey=MIFYHUACUWQUKT-GPUHXXMPSA-N

InChI=1S/C14H21N3O6S/c1-14(2)9(13(22)23)17-10(19)8(11(17)24-14)16-7(18)5-3-4-6(15)12(20)21/h6,8-9,11H,3-5,15H2,1-2H3,(H,16,18)(H,20,21)(H,22,23)/t6-,8-,9+,11-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C14H21N3O6S
Molecular Weight	359.398
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4209314 | https://www.drugfuture.com/chemdata/penicillin-n.html

Adicillin (Penicillin N) is a penicillin derivative produced by Cephalosporium acremonium. Adicillin is dextrorotatory. Inactivated by penicillinase as is penicillin G, but differs from the common penicillin by its antibacterial activity and hydrophilic character. Active against Sarcina lutea, Proteus vulgaris, Salmonella typhimurium, Diplococcus pneumoniae. Shows practically no activity against B. subtilis and Staph. aureus. The toxicity is somewhat less than that of penicillin G, although penicillin N is excreted more slowly.

Approval Year

PubMed

Title	Date	PubMed
Carbon catabolite regulation of the conversion of penicillin N into cephalosporin C.	1983-06	6683720
Microbiological ring expansion of penicillin N.	1981-05	6974164
Syntheses of penicillin N, [6 alpha-3H]penicillin N and [10-14C,6 alpha-3H]penicillin N.	1980-03-15	7396842
Biosynthesis of penicillin N and cephalosporin C. Antibiotic production and other features of the metabolism of Cephalosporium sp.	1967-06	6069166

Patents

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:33:21 GMT 2025` Edited by `admin` on `Wed Apr 02 07:33:21 GMT 2025`
Record UNII	NOF9U9EYQ4
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ADICILLIN

Official Name

English

NSC-113137

Preferred Name

English

adicillin [INN]

Common Name

English

6-(5-Amino-5-carboxyvaleramido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Systematic Name

English

(4-AMINO-4-CARBOXYBUTYL)PENICILLIN

Common Name

English

ADICILLIN [MART.]

Common Name

English

PENICILLIN N [MI]

Common Name

English

Adicillin [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1500