TIGECYCLINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H39N5O8
Molecular Weight	585.6487
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@@]12CC3=C(C=C(NC(=O)CNC(C)(C)C)C(O)=C3C(=O)C1=C(O)[C@]4(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]4([H])C2)N(C)C

InChI

InChIKey=FPZLLRFZJZRHSY-HJYUBDRYSA-N

InChI=1S/C29H39N5O8/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36/h10,12,14,21,31,36,38-39,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21-,29-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C29H39N5O8
Molecular Weight	585.6487
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Approval Year

Substance Class	Chemical
Record UNII	70JE2N95KR
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

TIGECYCLINE

Official Name

English

Tigecycline [WHO-DD]

Common Name

English

TIGECYCLINE [USAN]

Common Name

English

TIGECYCLINE [USP-RS]

Common Name

English

TIGECYCLINE [USP MONOGRAPH]

Common Name

English

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Classification Tree

Code System

Code

Tetracyclines

WHO-ATC

J01AA12

Naphthacenes

NDF-RT

N0000007948

Established Pharmacologic Class

NDF-RT

N0000175938

Tetracyclines

WHO-VATC

QJ01AA12

Designated

FDA ORPHAN DRUG

406313

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Code System

Code

Type

Description

CAS

220620-09-7

PRIMARY

MESH

C119092

PRIMARY

EPA CompTox

DTXSID2048581

PRIMARY

LACTMED

Tigecycline

PRIMARY

INN

8115

PRIMARY

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Related Record

Type

Details


					U98SS1SU9R

TIGECYCLINE, (4R)-

DEGRADENT -> PARENT

Amount:


					514B9K0L10

ESCHERICHIA COLI

TARGET ORGANISM->INHIBITOR

Amount:


					7F4TZ17Y3R

TIGECYCLINE HYDROCHLORIDE

SALT/SOLVATE -> PARENT

Amount:


					70JE2N95KR

TIGECYCLINE

EXCRETED UNCHANGED

Qualification:

URINE

Amount:

22 % (average)


					15E04LZ9CT

ENTEROCOCCUS FAECALIS

TARGET ORGANISM->INHIBITOR

Amount:

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Type

Details


					W0778NOJ5H

9-AMINOMINOCYCLINE

METABOLITE -> PARENT

Comments:

Trace amount; demonstrated some antibacterial activity in vitro, their activities were generally less than that of tigecycline and were effective against a narrower range of infectious organisms (data on file at Wyeth Research)

Interaction Type:

MINOR

Qualification:

PLASMA; URINE

Amount:


					63Y3VCE252

TIGECYCLINE GLUCURONIDE, (4R)-

METABOLITE -> PARENT

Interaction Type:

MINOR

Qualification:

FECAL; PLASMA

Amount:


					5DDZ7K1TCR

9-(N-ACETYLAMINO)MINOCYCLINE

METABOLITE -> PARENT

Comments:

Although both M5 and M6 demonstrated some antibac- terial activity in vitro, their activities were generally less than that of tigecycline and were effective against a narrower range of infectious organisms (data on file at Wyeth Research).

Qualification:

PLASMA; URINE

Amount:


					C38H031Q86

N-TERT-BUTYLGLYCINE

METABOLITE -> PARENT

Interaction Type:

MAJOR

Qualification:

FECAL; PLASMA; URINE

Amount:


					D1M8CF98S8

TIGECYCLINE GLUCURONIDE

METABOLITE -> PARENT

Comments:

Major peak in feces

Interaction Type:

MAJOR

Qualification:

FECAL; PLASMA; URINE

Amount:

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Type

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					U98SS1SU9R

TIGECYCLINE, (4R)-

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

WEIGHT PERCENT [<0.6] % (limits)


					FYY3R43WGO

MINOCYCLINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

WEIGHT PERCENT [<0.2] % (limits)


					W0778NOJ5H

9-AMINOMINOCYCLINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

WEIGHT PERCENT [<0.15] % (limits)


					EEJ33M2LLB

(4S,4AS,5AR,12AS)-9-AMINO-4,7-BIS(DIMETHYLAMINO)-3,10,12,12A-TETRAHYDROXY-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDROTETRACENE-2-CARBOXAMIDE HYDROCHLORIDE

IMPURITY -> PARENT

Amount:

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Type

Details


					70JE2N95KR

TIGECYCLINE

ACTIVE MOIETY

Amount:

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Name	Property Type	Amount	Parameters
Biological Half-life	PHARMACOKINETIC	55.8 hours (average)	INTRAVENOUS ADMINISTRATION SINGLE DOSE 50 mg (average)

Volume of Distribution	PHARMACOKINETIC	[7 to 9] Liters/Kilogram (average)	AT STEADY-STATE