TRAMADOL

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H25NO2
Molecular Weight	263.3752
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

COC1=CC=CC(=C1)[C@@]2(O)CCCC[C@@H]2CN(C)C

InChI

InChIKey=TVYLLZQTGLZFBW-ZBFHGGJFSA-N

InChI=1S/C16H25NO2/c1-17(2)12-14-7-4-5-10-16(14,18)13-8-6-9-15(11-13)19-3/h6,8-9,11,14,18H,4-5,7,10,12H2,1-3H3/t14-,16+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C16H25NO2
Molecular Weight	263.3752
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical
Record UNII	39J1LGJ30J
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

TRAMADOL

Official Name

English

E-265

Code

English

ETS6103

Code

English

(±)-TRAMADOL

Common Name

English

(±)-CIS-2-((DIMETHYLAMINO)METHYL)-1-(M-METHOXYPHENYL)CYCLOHEXANOL

Common Name

English

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Classification Tree

Code System

Code

Other opioids

WHO-VATC

QN02AX02

Other opioids

WHO-ATC

N02AX02

Opioids in combination with non-opioid analgesics

WHO-ATC

N02AJ13

Sec. 1308.11 Schedule IV.

DEA NO.

9278

Opioid Agonists

NDF-RT

N0000175684

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Code System

Code

Type

Description

ChEMBL

CHEMBL1237044

PRIMARY

SMS_ID

100000077198

PRIMARY

WIKIPEDIA

TRAMADOL

PRIMARY

ECHA (EC/EINECS)

248-319-6

PRIMARY

PUBCHEM

33741

PRIMARY

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Type

Details


					HN86OLH1NW

SODIUM-DEPENDENT NORADRENALINE TRANSPORTER

TARGET -> INHIBITOR

Comments:

(−)-tramadol inhibits norepinephrine reuptake

Amount:


					26J30IC20Q

TRAMADOL, (-)-

ENANTIOMER -> RACEMATE

Amount:


					EFC42N2AU4

CELECOXIB TRAMADOL HYDROBROMIDE CO-CRYSTAL

SALT/SOLVATE -> PARENT

Amount:


					VK4SQL11C0

CYTOCHROME P450 1A2

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

MINOR

Amount:


					1PE72K8X46

MU-TYPE OPIOID RECEPTOR

TARGET -> AGONIST

Comments:

(+)-isomer

Interaction Type:

COMPETITIVE INHIBITOR

Qualification:

Ki

Amount:

2400 NANOMOLAR (average)
NALOXONE COMPETITOR

Showing 1 to 5 of 16 entries

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Type

Details


					2WA8F50C3F

DESMETRAMADOL

METABOLITE ACTIVE -> PRODRUG

Amount:


					SRZ6938M82

N,N,O-TRIDEMETHYLTRAMADOL

METABOLITE -> PARENT

Interaction Type:

MINOR

Amount:


					8M7YSN2KII

N-DESMETHYLTRAMADOL

METABOLITE -> PARENT

Interaction Type:

MAJOR

Amount:


					XDX4ZNH4WE

CYCLOHEXANOL, 2-(AMINOMETHYL)-1-(3-METHOXYPHENYL)-, CIS-

METABOLITE -> PARENT

Interaction Type:

MINOR

Amount:


					F6F6QC876T

O,N-DIDESMETHYLTRAMADOL

METABOLITE ACTIVE -> PRODRUG

Amount:

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Type

Details


					39J1LGJ30J

TRAMADOL

ACTIVE MOIETY

Amount:

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Name	Property Type	Amount	Parameters
Route of Elimination	PHARMACOKINETIC	MOLE PERCENT OF AMOUNT EXCRETED 60 % (average) AS METABOLITE, RENAL	EXCRETED UNCHANGED, RENAL PHARMACOKINETIC MOLE PERCENT OF AMOUNT EXCRETED 30 % (average)

ORAL BIOAVAILABILITY	PHARMACOKINETIC	MOLE PERCENT OF AMOUNT ADMINISTERED 75 % (average) IMMEDIATE-RELEASE TABLET	EXTENDED-RELEASE TABLET PHARMACOKINETIC MOLE PERCENT OF AMOUNT ADMINISTERED [85 to 95] % (average) RELATIVE TO IMMEDIATE-RELEASE TABLET

MAXIMUM TOLERATED DOSE	TOXICITY	300 mg/day (average) ORAL EXTENDED-RELEASE TABLET	IMMEDIATE-RELEASE TABLET 400 mg/day (average)

Route of Elimination	PHARMACOKINETIC	MOLE PERCENT OF AMOUNT EXCRETED 60 % (average) AS METABOLITE	PERCENT EXCRETED UNCHANGED PHARMACOKINETIC MOLE PERCENT OF AMOUNT EXCRETED 30 % (average)

Tmax	PHARMACOKINETIC	[4 to 12] hours (average) ORAL, EXTENDED-RELEASE TABLET	EFFECT OF FOOD PHARMACOKINETIC INCREASED 3 HOURS

Volume of Distribution	PHARMACOKINETIC	2.9 Liters/Kilogram (average) FEMALE	MALE PHARMACOKINETIC 2.6 Liters/Kilogram (average)

PROTEIN BINDING	PHARMACOKINETIC	MOLE PERCENT OF AMOUNT ADMINISTERED 20 % (average)

Tmax	PHARMACOKINETIC	[1 to 2.3] hours (average) ORAL, IMMEDIATE-RELEASE TABLET	ORAL, IMMEDIATE-RELEASE TABLET (GERIATRICS) PHARMACOKINETIC 2.1 hours (average) ORAL, IMMEDIATE-RELEASE TABLET (HEPATIC IMPAIRMENT) PHARMACOKINETIC 1.9 hours (average)

Biological Half-life	PHARMACOKINETIC	[5.6 to 6.7] hours (average) IMMEDIATE-RELEASE, ADULTS	IMMEDIATE-RELEASE (GERIATRIC 75 YEARS AND OLDER) PHARMACOKINETIC 7 hours (average) O-DESMETHYL-TRAMADOL (M1), IMMEDIATE-RELEASE PHARMACOKINETIC [6.7 to 7] (average) IMMEDIATE-RELEASE IMMEDIATE-RELEASE (HEPATIC IMPAIRMENT) PHARMACOKINETIC 13 hours (average) IV, RENAL IMPAIRMENT (CrCL LESS THAN 30 mL/min) PHARMACOKINETIC [10.6 to 11] hours (average) O-DESMETHYL-TRAMADOL (M1), EXTENDED-RELEASE PHARMACOKINETIC [7.5 to 11] hours (average) EXTENDED-RELEASE PHARMACOKINETIC [6.5 to 10] hours (average) O-DESMETHYL-TRAMADOL (M1), IMMEDIATE-RELEASE (HEPATIC IMPAIRMENT) PHARMACOKINETIC [18.5 to 19] hours (average) O-DESMETHYL-TRAMADOL (M1), IV, RENAL IMPAIRMENT (CrCL LESS THAN 30 mL/min) PHARMACOKINETIC [11.5 to 16.9] hours (average)