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Details

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

SHOW SMILES / InChI
Structure of TRAMADOL, (+)-

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

Description
Curator's Comment: description was created based on several sources, including https://www.drugs.com/tramadol.html | https://www.drugbank.ca/drugs/DB00193 | http://reference.medscape.com/drug/ultram-er-tramadol-343324 |

Tramadol (sold under the brand name Ultram) is a narcotic analgesic proposed for moderate to severe pain. Tramadol and its O-desmethyl metabolite (M1) are selective, weak OP3-receptor agonists. Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine, and noradrenaline is inhibited. The analgesic properties of Tramadol can be attributed to norepinephrine and serotonin reuptake blockade in the CNS, which inhibits pain transmission in the spinal cord. The (+) enantiomer has the higher affinity for the OP3 receptor and preferentially inhibits serotonin uptake and enhances serotonin release. The (-) enantiomer preferentially inhibits norepinephrine reuptake by stimulating alpha(2)-adrenergic receptors. Tramadol is used primarily to treat mild-severe pain, both acute and chronic. Its analgesic effects take about one hour to come into effect and 2 h to 4 h to peak after oral administration with an immediate-release formulation. On a dose-by-dose basis, tramadol has about one-tenth the potency of morphine and is approximately equally potent when compared to pethidine and codeine. The most common adverse effects of tramadol include nausea, dizziness, dry mouth, indigestion, abdominal pain, vertigo, vomiting, constipation, drowsiness, and headache. Compared to other opioids, respiratory depression and constipation are considered less of a problem with tramadol.

Originator

Sources: Oyo Yakuri (1973), 7, (7), 1087-95.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1300.0 nM [EC50]
14.0 nM [Ki]
9.4 nM [Ki]
1493.0 nM [IC50]
3861.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ULTRAM

Approved Use

Tramadol hydrochloride extended-release tablets are indicated for the management of moderate to moderately severe chronic pain in adults who require around-the-clock treatment of their pain for an extended period of time.

Launch Date

7.9418878E11
Primary
ULTRAM

Approved Use

Tramadol hydrochloride extended-release tablets are indicated for the management of moderate to moderately severe chronic pain in adults who require around-the-clock treatment of their pain for an extended period of time.

Launch Date

7.9418878E11
Primary
ULTRAM

Approved Use

Tramadol hydrochloride extended-release tablets are indicated for the management of moderate to moderately severe chronic pain in adults who require around-the-clock treatment of their pain for an extended period of time.

Launch Date

7.9418878E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
332 ng/mL
200 mg 1 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TRAMADOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
70 ng/mL
200 mg 1 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
O-DESMETHYLTRAMADOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
5678 ng × h/mL
200 mg 1 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TRAMADOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
1319 ng × h/mL
200 mg 1 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
O-DESMETHYLTRAMADOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
80%
200 mg 1 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TRAMADOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
600 mg 1 times / day multiple, oral
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
healthy, 28
n = 8
Health Status: healthy
Age Group: 28
Sex: M+F
Population Size: 8
Sources:
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea (75%)
Vomiting (50%)
Headache (25%)
Dizziness postural (25%)
Vertigo (25%)
Dizziness (12.5%)
Pruritus (37.5%)
Decreased appetite (25%)
Hot flush (12.5%)
Sources:
1500 mg single, oral (median)
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources:
unknown, 41
n = 359
Health Status: unknown
Age Group: 41
Sex: M+F
Population Size: 359
Sources:
Other AEs: Seizure, Nausea and vomiting...
Other AEs:
Seizure (14.5%)
Nausea and vomiting (53.5%)
Tachycardia (4.8%)
Hypertension (mild, 38.4%)
Arrhythmia (5.3%)
Sources:
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
n = 1054
Health Status: unhealthy
Condition: osteoarthritis
Age Group: adult
Population Size: 1054
Sources:
Other AEs: Dry mouth, Sweating...
Other AEs:
Dry mouth (13.1%)
Sweating (6.7%)
Asthenia (8.6%)
Pruritus (7.3%)
Arthralgia (5%)
Headache (19%)
Nausea (25.1%)
Somnolence (16.1%)
Dizziness (13.6%)
Constipation (21.3%)
Vomiting (9.3%)
Anorexia (5.7%)
Insomnia (5%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Dizziness 12.5%
600 mg 1 times / day multiple, oral
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
healthy, 28
n = 8
Health Status: healthy
Age Group: 28
Sex: M+F
Population Size: 8
Sources:
Hot flush 12.5%
600 mg 1 times / day multiple, oral
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
healthy, 28
n = 8
Health Status: healthy
Age Group: 28
Sex: M+F
Population Size: 8
Sources:
Decreased appetite 25%
600 mg 1 times / day multiple, oral
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
healthy, 28
n = 8
Health Status: healthy
Age Group: 28
Sex: M+F
Population Size: 8
Sources:
Dizziness postural 25%
600 mg 1 times / day multiple, oral
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
healthy, 28
n = 8
Health Status: healthy
Age Group: 28
Sex: M+F
Population Size: 8
Sources:
Headache 25%
600 mg 1 times / day multiple, oral
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
healthy, 28
n = 8
Health Status: healthy
Age Group: 28
Sex: M+F
Population Size: 8
Sources:
Vertigo 25%
600 mg 1 times / day multiple, oral
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
healthy, 28
n = 8
Health Status: healthy
Age Group: 28
Sex: M+F
Population Size: 8
Sources:
Pruritus 37.5%
600 mg 1 times / day multiple, oral
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
healthy, 28
n = 8
Health Status: healthy
Age Group: 28
Sex: M+F
Population Size: 8
Sources:
Vomiting 50%
600 mg 1 times / day multiple, oral
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
healthy, 28
n = 8
Health Status: healthy
Age Group: 28
Sex: M+F
Population Size: 8
Sources:
Nausea 75%
600 mg 1 times / day multiple, oral
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
healthy, 28
n = 8
Health Status: healthy
Age Group: 28
Sex: M+F
Population Size: 8
Sources:
Seizure 14.5%
1500 mg single, oral (median)
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources:
unknown, 41
n = 359
Health Status: unknown
Age Group: 41
Sex: M+F
Population Size: 359
Sources:
Tachycardia 4.8%
1500 mg single, oral (median)
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources:
unknown, 41
n = 359
Health Status: unknown
Age Group: 41
Sex: M+F
Population Size: 359
Sources:
Arrhythmia 5.3%
1500 mg single, oral (median)
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources:
unknown, 41
n = 359
Health Status: unknown
Age Group: 41
Sex: M+F
Population Size: 359
Sources:
Nausea and vomiting 53.5%
1500 mg single, oral (median)
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources:
unknown, 41
n = 359
Health Status: unknown
Age Group: 41
Sex: M+F
Population Size: 359
Sources:
Hypertension mild, 38.4%
1500 mg single, oral (median)
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources:
unknown, 41
n = 359
Health Status: unknown
Age Group: 41
Sex: M+F
Population Size: 359
Sources:
Dry mouth 13.1%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
n = 1054
Health Status: unhealthy
Condition: osteoarthritis
Age Group: adult
Population Size: 1054
Sources:
Dizziness 13.6%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
n = 1054
Health Status: unhealthy
Condition: osteoarthritis
Age Group: adult
Population Size: 1054
Sources:
Somnolence 16.1%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
n = 1054
Health Status: unhealthy
Condition: osteoarthritis
Age Group: adult
Population Size: 1054
Sources:
Headache 19%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
n = 1054
Health Status: unhealthy
Condition: osteoarthritis
Age Group: adult
Population Size: 1054
Sources:
Constipation 21.3%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
n = 1054
Health Status: unhealthy
Condition: osteoarthritis
Age Group: adult
Population Size: 1054
Sources:
Nausea 25.1%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
n = 1054
Health Status: unhealthy
Condition: osteoarthritis
Age Group: adult
Population Size: 1054
Sources:
Arthralgia 5%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
n = 1054
Health Status: unhealthy
Condition: osteoarthritis
Age Group: adult
Population Size: 1054
Sources:
Insomnia 5%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
n = 1054
Health Status: unhealthy
Condition: osteoarthritis
Age Group: adult
Population Size: 1054
Sources:
Anorexia 5.7%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
n = 1054
Health Status: unhealthy
Condition: osteoarthritis
Age Group: adult
Population Size: 1054
Sources:
Sweating 6.7%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
n = 1054
Health Status: unhealthy
Condition: osteoarthritis
Age Group: adult
Population Size: 1054
Sources:
Pruritus 7.3%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
n = 1054
Health Status: unhealthy
Condition: osteoarthritis
Age Group: adult
Population Size: 1054
Sources:
Asthenia 8.6%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
n = 1054
Health Status: unhealthy
Condition: osteoarthritis
Age Group: adult
Population Size: 1054
Sources:
Vomiting 9.3%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
n = 1054
Health Status: unhealthy
Condition: osteoarthritis
Age Group: adult
Population Size: 1054
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
unlikely
yes
yes
likely (co-administration study)
Comment: Coadministration of quinidine, a selective inhibitor of CYP2D6, with tramadol ER resulted in a 50­ 60% increase in tramadol exposure; pharmacogenomic studies were also conducted: rapid conversion to active metabolite results in higher than expected serum M1 levels. Individuals who are ultra-rapid metabolizers should not use drug.
Page: 5.0
yes
likely (co-administration study)
Comment: The concomitant use of ULTRAM with cytochrome P450 3A4 inhibitors, such as macrolide antibiotics (e.g., erythromycin), azole-antifungal agents (e.g., ketoconazole), and protease inhibitors (e.g., ritonavir) or discontinuation of a cytochrome P450 3A4 inducer such as rifampin, carbamazepine, and phenytoin, may result in an increase in tramadol plasma concentrations; Concomitant administration of tramadol immediate-release tablets with cimetidine, a weak CPY3A4 inhibitor, does not result in clinically significant changes in tramadol pharmacokinetics;
Page: 5.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Interactions between systemic analgesics.
2001
Control of non-malignant chronic pain conditions in Japan and the possible future role of tramadol.
2001
Single-dose dipyrone for acute postoperative pain.
2001
Analgesic efficacy of tramadol 2 mg kg(-1) for paediatric day-case adenoidectomy.
2001 Apr
A nonsurgical approach to low back pain.
2001 Apr
[Control of postoperative pain in heart surgery. Comparison of analgesics].
2001 Apr
[Factors affecting postoperative pain].
2001 Apr
Tramadol for postoperative shivering: a double-blind comparison with pethidine.
2001 Apr
[Sensory neuropathy in HIV infection: pathogenesis and therapy].
2001 Apr 14
Pharmacology of oral combination analgesics: rational therapy for pain.
2001 Aug
Identification of cytochrome P-450 isoforms responsible for cis-tramadol metabolism in human liver microsomes.
2001 Aug
Nefopam reduces thermal hypersensitivity in acute and postoperative pain models in the rat.
2001 Dec
Analgesic efficacy of tramadol if coadministered with ondansetron.
2001 Dec
Plasma glucose-lowering effect of tramadol in streptozotocin-induced diabetic rats.
2001 Dec
Pharmacokinetics of enantiomers of trans-tramadol and its active metabolite, trans-O-demethyltramadol, in human subjects.
2001 Jan
Comparison of caudal morphine and tramadol for postoperative pain control in children undergoing inguinal herniorrhaphy.
2001 Jul
Caudal bupivacaine-tramadol combination for postoperative analgesia in pediatric herniorrhaphy.
2001 Jul
[Analysis of prehospital analgesia administered to victims with traumatic injuries].
2001 Jul-Aug
[Chronic pain in geriatrics].
2001 Jun
Anesthetic considerations in a patient with visceral leishmaniasis.
2001 Jun
Tramadol dependence with no history of substance abuse.
2001 Jun
Mania and tramadol-fluoxetine combination.
2001 Jun
Direct tramadol application on sciatic nerve inhibits spinal somatosensory evoked potentials in rats.
2001 Jun
Tramadol, an alternative to morphine for treating posttraumatic pain in the prehospital situation.
2001 Jun
Pharmacologic treatment of neuropathic pain.
2001 Mar
Treatment of refractory major depression with tramadol monotherapy.
2001 Mar
Abuse of combinations of carisoprodol and tramadol.
2001 May
The analgesic efficacy of tramadol is impaired by concurrent administration of ondansetron.
2001 May
Effects of tramadol on T lymphocyte proliferation and natural killer cell activity in rats with sciatic constriction injury.
2001 May
A comparison of tramadol, amitriptyline, and meperidine for postepidural anesthetic shivering in parturients.
2001 Nov
Gas chromatographic method using nitrogen-phosphorus detection for the measurement of tramadol and its O-desmethyl metabolite in plasma and brain tissue of mice and rats.
2001 Nov 5
Acetaminophen, aspirin, or Ibuprofen in combination analgesic products.
2001 Nov-Dec
Urinary disorders on tramadol.
2001 Oct
Distribution of enantiomers of trans-tramadol and trans-O-demethyltramadol in central nervous system of rats.
2001 Oct
Inhibition by tramadol of muscarinic receptor-induced responses in cultured adrenal medullary cells and in Xenopus laevis oocytes expressing cloned M1 receptors.
2001 Oct
Multidimensional on-line solid-phase extraction (SPE) using restricted access materials (RAM) in combination with molecular imprinted polymers (MIP).
2001 Sep
Intravenous regional anaesthesia using lignocaine and tramadol.
2001 Sep
Tramadol/acetaminophen combination tablets and codeine/acetaminophen combination capsules for the management of chronic pain: a comparative trial.
2001 Sep
Effects of chronic tramadol on pre- and post-synaptic measures of monoamine function.
2001 Sep
[Non-opioid analgesics in cancer pain].
2001 Sep
Psychosomatic reactions to a stressful environment and an attempt at pharmacological modification.
2001 Sep-Oct
Tramadol and acetaminophen tablets for dental pain.
2001 Summer
New, non-NSAID alternative.
2002 Feb
The addition of tramadol to lidocaine does not reduce tourniquet and postoperative pain during iv regional anesthesia.
2002 Feb
Pharmacological treatment of postoperative shivering: a quantitative systematic review of randomized controlled trials.
2002 Feb
The role of tricyclic antidepressants and tramadol in palliative care.
2002 Feb
Stereoselectivity in renal clearance of trans-tramadol and its active metabolite, trans-O-demethyltramadol.
2002 Jan
Concordance between tramadol and dextromethorphan parent/metabolite ratios: the influence of CYP2D6 and non-CYP2D6 pathways on biotransformation.
2002 Jan
Physical compatibility and in vivo evaluation of drug mixtures for subcutaneous infusion to cancer patients in palliative care.
2002 Jan
Meeting the therapeutic challenge of the patient with osteoarthritis.
2002 Jan-Feb
Patents

Sample Use Guides

Chronic: 25 mg PO every morning initially; increased by 25-50 mg/day every 3 days up to 50-100 mg PO q4-6hr PRN; not to exceed 400 mg/day Acute: 50-100 mg PO q4-6hr PRN; not to exceed 400 mg/day
Route of Administration: Oral
A malignancy of A549 and PC-9 cells was detected after treatment of 2 μM tramadol for different time (0, 7, 14, or 28 d). The effect of tramadol on the invasion of A549 and PC-9 cells was performed using transwell chambers (6.5 mm diameter and 8 μm pore size; Millipore, Billerica, MA, USA). After treated with 2 μM tramadol for various time, cells were plated onto the Matrigel-coated upper part of the transwell chamber, fetal bovine serum (FBS) medium (20%) was added to the lower wells as a chemoattractant. 48 hours later, non-invading cells were removed, the invaded cells were fixed with 4% paraformaldehyde for 30 min and stained with 1% crystal violet for 30 min. The number of stained cells on the undersurface of the polycarbonate membranes was then counted visually in five random image fields at 200 × magnifications using a microscope (Olympus, Lake Success, NY, USA).
Substance Class Chemical
Created
by admin
on Sun Dec 18 04:38:14 UTC 2022
Edited
by admin
on Sun Dec 18 04:38:14 UTC 2022
Record UNII
0NG5TTM63P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRAMADOL, (+)-
Common Name English
(+)-(R,R)-TRAMADOL
Common Name English
(1R,2R)-2-((DIMETHYLAMINO)METHYL)-1-(3-METHOXYPHENYL)CYCLOHEXANOL
Common Name English
(+)-TRAMADOL
Common Name English
Code System Code Type Description
PUBCHEM
33741
Created by admin on Sun Dec 18 04:38:15 UTC 2022 , Edited by admin on Sun Dec 18 04:38:15 UTC 2022
PRIMARY
CHEBI
75725
Created by admin on Sun Dec 18 04:38:15 UTC 2022 , Edited by admin on Sun Dec 18 04:38:15 UTC 2022
PRIMARY
CAS
123154-38-1
Created by admin on Sun Dec 18 04:38:15 UTC 2022 , Edited by admin on Sun Dec 18 04:38:15 UTC 2022
PRIMARY
FDA UNII
0NG5TTM63P
Created by admin on Sun Dec 18 04:38:15 UTC 2022 , Edited by admin on Sun Dec 18 04:38:15 UTC 2022
PRIMARY
Related Record Type Details
TARGET -> AGONIST
TARGET -> INHIBITOR
ENANTIOMER -> ENANTIOMER
RACEMATE -> ENANTIOMER
Agonist of the ?. opioid receptor and inhibits serotonin reuptake.