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

Details

Stereochemistry ABSOLUTE
Molecular Formula C44H60N4O12
Molecular Weight 836.9668
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of RIFAMETANE

SMILES

CCN(CC)C(\C)=N\N=C\C1=C(O)C2=C3C(=O)[C@]4(C)OC3=C(C)C(O)=C2C(O)=C1NC(=O)C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O4

InChI

InChIKey=MPNLXDYNHVIMAT-WDJJWENTSA-N
InChI=1S/C44H60N4O12/c1-13-48(14-2)27(9)47-45-20-29-34-39(54)32-31(38(29)53)33-41(26(8)37(32)52)60-44(11,42(33)55)58-19-18-30(57-12)23(5)40(59-28(10)49)25(7)36(51)24(6)35(50)21(3)16-15-17-22(4)43(56)46-34/h15-21,23-25,30,35-36,40,50-54H,13-14H2,1-12H3,(H,46,56)/b16-15+,19-18+,22-17-,45-20+,47-27+/t21-,23+,24+,25+,30-,35-,36+,40+,44-/m0/s1

HIDE SMILES / InChI

Molecular Formula C44H60N4O12
Molecular Weight 836.9668
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 2
Optical Activity UNSPECIFIED

Rifametane (SPA-S-565) is a semisynthetic derivative of rifamycin (a natural antibiotic produced by Amycolatopsis rifamycinica). It was being evaluated for treatment of bacterial infections. A phase I study showed that administration of rifametane is safe with minor, reversible adverse events such as mild headache, metallic taste and slightly elevated temperature for 3 to 4 hours. Rifametane has anti-tuberculosis activity and was suggested to be a good candidate for phase II clinical trials.

Originator

Approval Year

Substance Class Chemical
Created
by admin
on Fri Dec 15 16:03:50 GMT 2023
Edited
by admin
on Fri Dec 15 16:03:50 GMT 2023
Record UNII
1PUG6262HX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RIFAMETANE
INN   USAN  
USAN   INN  
Official Name English
(2S,12Z,14E,16S,17S,18R,19R,20R,21S,22S,23S,24E)-1,2-Dihydro-5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-8-carboxyaldehyde, 8-azine with N,N-diethylacetamide,
Systematic Name English
rifametane [INN]
Common Name English
RIFAMETANE [USAN]
Common Name English
SPA-S-565
Code English
RIFAMYCIN, 3-(((1-(DIETHYLAMINO)ETHYLIDENE)HYDRAZONO)METHYL)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C280
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
Code System Code Type Description
USAN
Z-17
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
SMS_ID
100000080579
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
EVMPD
SUB10306MIG
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
PUBCHEM
135475446
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
FDA UNII
1PUG6262HX
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
ChEMBL
CHEMBL2103938
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
CAS
94168-98-6
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
INN
6435
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
MESH
C058615
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
NCI_THESAURUS
C90771
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY