ANTHRAMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H17N3O4
Molecular Weight	315.3239
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C2C(N[C@H](O)[C@@H]3CC(\C=C\C(N)=O)=CN3C2=O)=C1O

InChI

InChIKey=VGQOVCHZGQWAOI-YQRHFANHSA-N

InChI=1S/C16H17N3O4/c1-8-2-4-10-13(14(8)21)18-15(22)11-6-9(3-5-12(17)20)7-19(11)16(10)23/h2-5,7,11,15,18,21-22H,6H2,1H3,(H2,17,20)/b5-3+/t11-,15+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C16H17N3O4
Molecular Weight	315.3239
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/68000876 | https://www.ncbi.nlm.nih.gov/pubmed/5845427 | https://www.ncbi.nlm.nih.gov/pubmed/4959850

ANTHRAMYCIN, a member of the pyrolobenzodiazepine family, is an antineoplastic antibiotic derived from a thermophilic actinomycete Streptomyces refuineus var. thermotolerans (NRRL 3143). It binds covalently to DNA, thereby inhibiting replication and transcription processes.

Originator

Approval Year

PubMed

Title	Date	PubMed
Chemotherapeutic properities of anthramycin.	1966	4959850
Isolation and characterization of anthramycin, a new antitumor antibiotic.	1965-12-20	5845427
The structure of anthramycin.	1965-12-20	5845428

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:13:37 GMT 2025` Edited by `admin` on `Wed Apr 02 09:13:37 GMT 2025`
Record UNII	0WZD9Y66WN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANTRAMYCIN

Preferred Name

English

ANTHRAMYCIN

Official Name

English

antramycin [INN]

Common Name

English

ANTHRAMYCIN [MI]

Common Name

English

Antramycin [WHO-DD]

Common Name

English

(E)-5,10,11,11a-Tetrahydro-9,11-dihydroxy-8-methyl-5-oxo-1H-pyrrolo[2,1-c][1,4]-benzodiazepine-2-acrylamide

Common Name

English

(2E)-3-((11R,11AS)-5,10,11,11A-TETRAHYDRO-9,11-DIHYDROXY-8-METHYL-5-OXO-1H-PYRROLO(2,1-C)(1,4)BENZODIAZEPIN-2-YL)-2-PROPENAMIDE

Common Name

English

2-PROPENAMIDE, 3-(5,10,11,11A-TETRAHYDRO-9,11-DIHYDROXY-8-METHYL-5-OXO-1H-PYRROLO(2,1-C)(1,4)BENZODIAZEPIN-2-YL)-, (E)-

Common Name

English

ANTHRAMYCIN [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2115