RIFAMIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C43H58N2O13
Molecular Weight	810.9262
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)C(=O)COC1=C2C3=C4O[C@](C)(O\C=C\[C@H](OC)[C@@H](C)[C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)C(=O)NC(=C1)C(O)=C2C(O)=C4C)C3=O

InChI

InChIKey=VFYNXKZVOUXHDX-VDPUEHCXSA-N

InChI=1S/C43H58N2O13/c1-12-45(13-2)31(47)20-55-30-19-28-38(51)33-32(30)34-40(26(8)37(33)50)58-43(10,41(34)52)56-18-17-29(54-11)23(5)39(57-27(9)46)25(7)36(49)24(6)35(48)21(3)15-14-16-22(4)42(53)44-28/h14-19,21,23-25,29,35-36,39,48-51H,12-13,20H2,1-11H3,(H,44,53)/b15-14+,18-17+,22-16-/t21-,23+,24+,25+,29-,35-,36+,39+,43-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C43H58N2O13
Molecular Weight	810.9262
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://dtb.bmj.com/content/6/22/86.long | https://academic.oup.com/jac/article/49/3/531/727573

Rifamides (NSC-143418) are drugs used in the treatment of tuberculosis. They also have immunosuppressive activity, the exact mechanism of which is still unknown, although the ability of rifamides to inhibit tumor necrosis factor (TNF)-induced NF-kB activation may be associated with it. A variety of rifamide analogues exist, such as rifamycin B, rifapentine, rifamycin SV, rifabutin and rifampicin.

Approval Year

PubMed

Title	Date	PubMed
In vitro bacteriological studies on rifamycin B diethylamide (rifamide).	1965 Jul	5898682
Desacetyl-rifamycins: preparation and antibacterial properties.	1968 Mar 15	4969311
Potentiation of rifampicin, rifampicin analogs, and tetracycline against animal cells by amphotericin B and polymyxin B.	1973 Jun	4352361

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:53:28 UTC 2023` Edited by `admin` on `Fri Dec 15 16:53:28 UTC 2023`
Record UNII	TS121H7U7E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RIFAMIDE

Official Name

English

RIFAMYCIN, 4-O-(2-(DIETHYLAMINO)-2-OXOETHYL)-

Common Name

English

NSC-143418

Code

English

2-((1,2-DIHYDRO-5,6,17,19,21-PENTAHYDROXY-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-9-YL)OXY)-N,N-DIETHYLACETAMIDE 21-ACETATE

Common Name

English

RIFAMYCIN B DIETHYLAMIDE

Common Name

English

RIFAMYCIN M-14

Code

English

RIFAMIDE [MI]

Common Name

English

NCI-143-418

Code

English

RIFOMYCIN M14

Common Name

English

Stereoisomer of N,N-Diethyl-2-[(1,2-dihydro-5,6,17,19,21-pentahydroxy-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-9-yl)oxy]acetamide 21-acetate

Common Name

English

rifamide [INN]

Common Name

English

NSC-133099

Code

English

RIFAMYCIN DIETHYLAMIDE

Common Name

English

4-O-(2-(DIETHYLAMINO)-2-OXOETHYL)-RIFAMYCIN

Common Name

English

RIFAMIDE [USAN]

Common Name

English

N,N-DIETHYLRIFOMYCIN B AMIDE

Common Name

English

RIFAMYCIN-M-14

Code

English

Rifamide [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C258