U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C29H38N4O9
Molecular Weight 586.6334
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPACYCLINE

SMILES

[H][C@@]12C[C@@]3([H])C(C(=O)C4=C(O)C=CC=C4[C@@]3(C)O)=C(O)[C@]1(O)C(=O)C(C(=O)NCN5CCN(CCO)CC5)=C(O)[C@H]2N(C)C

InChI

InChIKey=XATZHCXBMKRRDO-REHNUXHNSA-N
InChI=1S/C29H38N4O9/c1-28(41)15-5-4-6-18(35)19(15)23(36)20-16(28)13-17-22(31(2)3)24(37)21(26(39)29(17,42)25(20)38)27(40)30-14-33-9-7-32(8-10-33)11-12-34/h4-6,16-17,22,34-35,37-38,41-42H,7-14H2,1-3H3,(H,30,40)/t16-,17-,22-,28+,29-/m0/s1

HIDE SMILES / InChI
Pipacycline is a semi-synthetic tetracycline formed by a Mannich condensation of formaldehyde and 4-hydroxyethyl piperazine with tetracycline. The introduction of the piperazine improves bioavailability, but Mannich bases are pro-drugs, converting back to the parent compound. Pipacycline is used commercially as a salt in combination with penicillin V for parenteral use (penimepicycline). Penimepicycline exerts a bactericidal action on the streptococci, and a bacteriostatic action on various gram-positive and gram-negative bacilli, as well as on the penicillin-resistant staphylococci.

Approval Year

Name Type Language
PIPACYCLINE
INN   MI  
INN  
Official Name English
NSC-69335
Code English
4-DIMETHYLAMINO-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,6,10,12,12A-PENTA-HYDROXY-N-((4-(2-HYDROXYETHYL)-1-PIPERAZINYL)METHYL)-6-METHYL-1,11-DIOXO-2-NAPHTHACENECARBOXAMIDE
Common Name English
PIPACYCLINE [MI]
Common Name English
pipacycline [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1595
Created by admin on Fri Dec 15 16:11:19 GMT 2023 , Edited by admin on Fri Dec 15 16:11:19 GMT 2023
Code System Code Type Description
INN
1270
Created by admin on Fri Dec 15 16:11:19 GMT 2023 , Edited by admin on Fri Dec 15 16:11:19 GMT 2023
PRIMARY
NSC
69335
Created by admin on Fri Dec 15 16:11:19 GMT 2023 , Edited by admin on Fri Dec 15 16:11:19 GMT 2023
PRIMARY
NCI_THESAURUS
C66391
Created by admin on Fri Dec 15 16:11:19 GMT 2023 , Edited by admin on Fri Dec 15 16:11:19 GMT 2023
PRIMARY
SMS_ID
100000081960
Created by admin on Fri Dec 15 16:11:19 GMT 2023 , Edited by admin on Fri Dec 15 16:11:19 GMT 2023
PRIMARY
CHEBI
75262
Created by admin on Fri Dec 15 16:11:19 GMT 2023 , Edited by admin on Fri Dec 15 16:11:19 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105824
Created by admin on Fri Dec 15 16:11:19 GMT 2023 , Edited by admin on Fri Dec 15 16:11:19 GMT 2023
PRIMARY
FDA UNII
PQ3P6082I5
Created by admin on Fri Dec 15 16:11:19 GMT 2023 , Edited by admin on Fri Dec 15 16:11:19 GMT 2023
PRIMARY
CAS
1110-80-1
Created by admin on Fri Dec 15 16:11:19 GMT 2023 , Edited by admin on Fri Dec 15 16:11:19 GMT 2023
PRIMARY
ECHA (EC/EINECS)
214-176-3
Created by admin on Fri Dec 15 16:11:19 GMT 2023 , Edited by admin on Fri Dec 15 16:11:19 GMT 2023
PRIMARY
EVMPD
SUB09858MIG
Created by admin on Fri Dec 15 16:11:19 GMT 2023 , Edited by admin on Fri Dec 15 16:11:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID00891415
Created by admin on Fri Dec 15 16:11:19 GMT 2023 , Edited by admin on Fri Dec 15 16:11:19 GMT 2023
PRIMARY
MERCK INDEX
m8836
Created by admin on Fri Dec 15 16:11:19 GMT 2023 , Edited by admin on Fri Dec 15 16:11:19 GMT 2023
PRIMARY Merck Index