TAPENTADOL

Search structure
Trade Names:
Synonyms:
Status: Approved (2008)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N02AX06
UNII: H8A007M585

Structure
InChI Key KWTWDQCKEHXFFR-SMDDNHRTSA-N
Smile CC[C@@H](c1cccc(O)c1)[C@@H](C)CN(C)C
InChI
InChI=1S/C14H23NO/c1-5-14(11(2)10-15(3)4)12-7-6-8-13(16)9-12/h6-9,11,14,16H,5,10H2,1-4H3/t11-,14+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H23NO
Molecular Weight 221.34
AlogP 3.08
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 23.47
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 16.0

Pharmacology

Primary Target
μ receptor
NET
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Opioid receptor
670 - - 160 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 21890 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Neoplasms 3 D009369 ClinicalTrials
Neuralgia 3 D009437 ClinicalTrials
Diabetic Neuropathies 3 D003929 ClinicalTrials
Joint Diseases 3 D007592 ClinicalTrials
Back Pain 3 D001416 ClinicalTrials
Chronic Pain 3 D059350 ClinicalTrials
Osteoarthritis 3 D010003 ClinicalTrials
Hallux Valgus 3 D006215 ClinicalTrials
Low Back Pain 3 D017116 ClinicalTrials
Diabetic Neuropathies 3 D003929 ClinicalTrials
Osteoarthritis, Knee 3 D020370 ClinicalTrials
Osteoarthritis, Hip 3 D015207 ClinicalTrials

Related Entries

Salt

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Nausea 30.0
Gastrointestinal disorders Nausea 27.0
Cardiac disorders Dizziness 24.0
Gastrointestinal disorders Nausea 21.0
Cardiac disorders Dizziness 18.0
Gastrointestinal disorders Vomiting 18.0
Gastrointestinal disorders Constipation 17.0
Cardiac disorders Dizziness 17.0
Nervous system disorders Headache 15.0
Nervous system disorders Somnolence 15.0
Nervous system disorders Somnolence 14.0
Gastrointestinal disorders Constipation 13.0
Nervous system disorders Headache
Gastrointestinal disorders Nausea
Nervous system disorders Somnolence 12.0
Gastrointestinal disorders Vomiting 12.0
Nervous system disorders Headache 10.0
General disorders and administration site conditions Asthenia 9.0
General disorders and administration site conditions Fatigue 9.0
Gastrointestinal disorders Constipation 8.0
Cardiac disorders Dizziness
Gastrointestinal disorders Nausea
Skin and subcutaneous tissue disorders Pruritus 8.0
Gastrointestinal disorders Vomiting 8.0
Gastrointestinal disorders Constipation
Gastrointestinal disorders Diarrhoea 7.0
Gastrointestinal disorders Dry mouth 7.0
Gastrointestinal disorders Nausea
General disorders and administration site conditions Decreased appetite 6.0
Cardiac disorders Dizziness
Psychiatric disorders Anxiety 5.0
Gastrointestinal disorders Diarrhoea
Nervous system disorders Headache
General disorders and administration site conditions Hyperhidrosis 5.0
Skin and subcutaneous tissue disorders Pruritus 5.0
Psychiatric disorders Anxiety
General disorders and administration site conditions Asthenia
Gastrointestinal disorders Dry mouth 4.0
General disorders and administration site conditions Fatigue
Nervous system disorders Insomnia 4.0
Nervous system disorders Somnolence
Gastrointestinal disorders Vomiting
General disorders and administration site conditions Asthenia 3.0
Gastrointestinal disorders Constipation
Gastrointestinal disorders Dyspepsia 3.0
General disorders and administration site conditions Fatigue 3.0
General disorders and administration site conditions Hot flush 3.0
General disorders and administration site conditions Hyperhidrosis 3.0
Nervous system disorders Insomnia
Reproductive system and breast disorders Menopausal symptoms 3.0
Pruritus generalised 3.0
Nervous system disorders Somnolence
Nervous system disorders Tremor
Nervous system disorders Tremor 3.0
Gastrointestinal disorders Vomiting
Nervous system disorders Abnormal dreams 2.0
Psychiatric disorders Anxiety 2.0
General disorders and administration site conditions Asthenia 2.0
General disorders and administration site conditions Decreased appetite 2.0
Cardiac disorders Dizziness
Gastrointestinal disorders Dry mouth
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 2.0
General disorders and administration site conditions Hot flush
General disorders and administration site conditions Hot flush 2.0
General disorders and administration site conditions Hyperhidrosis
Nervous system disorders Insomnia
Nervous system disorders Insomnia 2.0
General disorders and administration site conditions Irritability 2.0
General disorders and administration site conditions Lethargy 2.0
Reproductive system and breast disorders Menopausal symptoms
Reproductive system and breast disorders Menopausal symptoms 2.0
Skin and subcutaneous tissue disorders Pruritus
Ear and labyrinth disorders Vertigo 2.0
Gastrointestinal disorders Abdominal discomfort
Gastrointestinal disorders Abdominal discomfort 1.0
Nervous system disorders Abnormal dreams
Nervous system disorders Abnormal dreams 1.0
Psychiatric disorders Anxiety
Psychiatric disorders Anxiety 1.0
Musculoskeletal and connective tissue disorders Arthralgia
Musculoskeletal and connective tissue disorders Arthralgia 1.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Chills
General disorders and administration site conditions Chills 1.0
Nervous system disorders Confusional state 1.0
Gastrointestinal disorders Constipation
General disorders and administration site conditions Decreased appetite
Psychiatric disorders Depression
Psychiatric disorders Depression 1.0
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Dermatitis 1.0
Nervous system disorders Disturbance in attention
Nervous system disorders Disturbance in attention 1.0
General disorders and administration site conditions Drug withdrawal syndrome
General disorders and administration site conditions Drug withdrawal syndrome 1.0
Gastrointestinal disorders Dry mouth
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 1.0
Cardiac disorders Dyspnoea 1.0
Psychiatric disorders Erectile dysfunction
Psychiatric disorders Erectile dysfunction 1.0
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Feeling abnormal 1.0
General disorders and administration site conditions Feeling hot
General disorders and administration site conditions Feeling hot 1.0
General disorders and administration site conditions Hot flush
General disorders and administration site conditions Hot flush 1.0
General disorders and administration site conditions Hyperhidrosis
Nervous system disorders Hypoaesthesia
Nervous system disorders Hypoaesthesia 1.0
Vascular disorders Hypotension
Vascular disorders Hypotension 1.0
Nervous system disorders Insomnia
General disorders and administration site conditions Irritability
General disorders and administration site conditions Lethargy
General disorders and administration site conditions Lethargy 1.0
Reproductive system and breast disorders Menopausal symptoms
Reproductive system and breast disorders Menopausal symptoms 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.0
Infections and infestations Nasopharyngitis
Infections and infestations Nasopharyngitis 1.0
Psychiatric disorders Nervousness 1.0
Skin and subcutaneous tissue disorders Pruritus
Pruritus generalised
Pruritus generalised 1.0
Skin and subcutaneous tissue disorders Rash
Skin and subcutaneous tissue disorders Rash 1.0
Nervous system disorders Somnolence
Psychiatric disorders Tension 1.0
Nervous system disorders Tremor
Nervous system disorders Tremor 1.0
Infections and infestations Upper respiratory tract infection
Infections and infestations Upper respiratory tract infection 1.0
Infections and infestations Urinary tract infection
Infections and infestations Urinary tract infection 1.0
Ear and labyrinth disorders Vertigo
Ear and labyrinth disorders Vertigo 1.0
Eye disorders Vision blurred
Eye disorders Vision blurred 1.0

Cross References

Resources Reference
CAS NUMBER 175591-23-8
ChEBI 135935
ChEMBL CHEMBL1201776
DrugBank DB06204
DrugCentral 4283
EPA CompTox DTXSID30170003
FDA SRS H8A007M585
Guide to Pharmacology 7477
PharmGKB PA166179720
PubChem 9838022
SureChEMBL SCHEMBL116924
ZINC ZINC000000020783
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