oxitriptan

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Stem definition	Drug id	CAS RN
serotonin (5-HT1) receptor agonists, sumatriptan derivatives	4006	4350-09-8

Stem definition

Drug id

CAS RN

serotonin (5-HT1) receptor agonists, sumatriptan derivatives

4006

4350-09-8

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: 5-Hydroxytryptophan triptene cincofarm hydroxytryptophan oxitriptan oxyfan pretonine levotinine levothym L-5-Hydroxytryptophan	5-HTP (5-Hydroxytryptophan) is a chemical by-product of the protein building block L-tryptophan. It is also produced commercially from the seeds of an African plant known as Griffonia simplicifolia 5-HTP is used for sleep disorders such as insomnia, depression, anxiety, migraine and tension-type headaches, fibromyalgia, obesity, premenstrual syndrome (PMS), premenstrual dysphoric disorder (PMDD), attention deficit-hyperactivity disorder (ADHD), seizure disorder, and Parkinson's disease. Molecular weight: 220.23 Formula: C11H12N2O3 CLOGP: -2.23 LIPINSKI: 0 HAC: 5 HDO: 4 TPSA: 99.34 ALOGS: -1.78 ROTB: 3

Molecule

Description

Molfile Inchi Smiles

Synonyms:

5-Hydroxytryptophan
triptene
cincofarm
hydroxytryptophan
oxitriptan
oxyfan
pretonine
levotinine
levothym
L-5-Hydroxytryptophan

5-HTP (5-Hydroxytryptophan) is a chemical by-product of the protein building block L-tryptophan. It is also produced commercially from the seeds of an African plant known as Griffonia simplicifolia 5-HTP is used for sleep disorders such as insomnia, depression, anxiety, migraine and tension-type headaches, fibromyalgia, obesity, premenstrual syndrome (PMS), premenstrual dysphoric disorder (PMDD), attention deficit-hyperactivity disorder (ADHD), seizure disorder, and Parkinson's disease.

Molecular weight: 220.23
Formula: C11H12N2O3
CLOGP: -2.23
LIPINSKI: 0
HAC: 5
HDO: 4
TPSA: 99.34
ALOGS: -1.78
ROTB: 3

Property	Value	Reference
BA (Bioavailability)	70 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.80 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	1.72 mL/min/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	6.14 hours	Lombardo F, Berellini G, Obach RS

Property

Value

Reference

BA (Bioavailability)

70 %

Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Vd (Volume of distribution)

0.80 L/kg

Lombardo F, Berellini G, Obach RS

CL (Clearance)

1.72 mL/min/kg

Lombardo F, Berellini G, Obach RS

t_half (Half-life)

6.14 hours

Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Property	Description	Value	Unit	Confidence	Similarity
azlogd74	LogD at pH 7.4	-1.514		Moderate	0.72
caco2-efflux	Caco-2 efflux ratio (BA/AB)	0.252		Moderate	0.72
caco2-intrinsic-papp	Caco-2 intrinsic apparent permeability	0.272	10^-6 cm/s	Moderate	0.72
dh-clint	Dog hepatocyte intrinsic clearance	1.028	uL/min/10^6 cells	Moderate	0.72
dppb	Dog plasma protein binding (% unbound)	73.050	%	Moderate	0.72
fcs-ppb	Fetal calf serum protein binding (% unbound)	68.230	%	Moderate	0.72
herg	hERG pIC50	4.579	pIC50	Moderate	0.72
hh-clint	Human hepatocyte intrinsic clearance	2.234	uL/min/10^6 cells	Moderate	0.72
hlm-clint	Human liver microsomal intrinsic clearance	3.793	uL/min/mg protein	Moderate	0.72
hppb	Human plasma protein binding (% unbound)	85.630	%	Moderate	0.72
kinase-safety-class	ACVR2A,ACVR2B,ACVRL1,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,ERBB2,FLT3,GRK2,GRK3,GSK3B,IKBKB,ITK,JAK1,JAK2,JAK3,KDR,KIT,MAP2K6,MAP3K14,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPK9,MAPKAPK2,MTOR,NTRK2,PDK1,PDK2,PDK4,PIK3CA,PIK3CB,PIM1,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ZAP70	56
kinase-selectivity-class	ACVR2B,AXL,CDK9,DYRK1B,EIF2AK3,GRK2,MAP2K6,TEK	8
mdck-mdr1-efflux	MDCK-MDR1 efflux ratio	0.521		Moderate	0.72
mh-clint	Mouse hepatocyte intrinsic clearance	2.128		Moderate	0.72
mppb	Mouse plasma protein binding (% unbound)	90.850		Moderate	0.72
nih-mdck-mdr1-efflux	NIH MDCK-MDR1 efflux ratio	0.323		Moderate	0.72
pfas-class	PFAS structural alert (1 = True, 0 = False)	0
pppb	Pig plasma protein binding (% unbound)	82.780	%	Moderate	0.72
rh-clint	Rat hepatocyte intrinsic clearance	1.014	uL/min/10^6 cells	Moderate	0.72
rh-fuinc	Rat hepatocyte fraction unbound in incubation	72.960	%	Moderate	0.72
rppb	Rat plasma protein binding (% unbound)	81.880	%	Moderate	0.72
solubility-dd	Solubility at pH 7.4 in DMSO	818.465	uM	Moderate	0.72

Property

Description

Value

Unit

Confidence

Similarity

azlogd74

LogD at pH 7.4

-1.514

Moderate

0.72

caco2-efflux

Caco-2 efflux ratio (BA/AB)

0.252

Moderate

0.72

caco2-intrinsic-papp

Caco-2 intrinsic apparent permeability

0.272

10^-6 cm/s

Moderate

0.72

dh-clint

Dog hepatocyte intrinsic clearance

1.028

uL/min/10^6 cells

Moderate

0.72

dppb

Dog plasma protein binding (% unbound)

73.050

Moderate

0.72

fcs-ppb

Fetal calf serum protein binding (% unbound)

68.230

Moderate

0.72

herg

hERG pIC50

4.579

pIC50

Moderate

0.72

hh-clint

Human hepatocyte intrinsic clearance

2.234

uL/min/10^6 cells

Moderate

0.72

hlm-clint

Human liver microsomal intrinsic clearance

3.793

uL/min/mg protein

Moderate

0.72

hppb

Human plasma protein binding (% unbound)

85.630

Moderate

0.72

kinase-safety-class

ACVR2A,ACVR2B,ACVRL1,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,ERBB2,FLT3,GRK2,GRK3,GSK3B,IKBKB,ITK,JAK1,JAK2,JAK3,KDR,KIT,MAP2K6,MAP3K14,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPK9,MAPKAPK2,MTOR,NTRK2,PDK1,PDK2,PDK4,PIK3CA,PIK3CB,PIM1,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ZAP70

kinase-selectivity-class

ACVR2B,AXL,CDK9,DYRK1B,EIF2AK3,GRK2,MAP2K6,TEK

mdck-mdr1-efflux

MDCK-MDR1 efflux ratio

0.521

Moderate

0.72

mh-clint

Mouse hepatocyte intrinsic clearance

2.128

Moderate

0.72

mppb

Mouse plasma protein binding (% unbound)

90.850

Moderate

0.72

nih-mdck-mdr1-efflux

NIH MDCK-MDR1 efflux ratio

0.323

Moderate

0.72

pfas-class

PFAS structural alert (1 = True, 0 = False)

pppb

Pig plasma protein binding (% unbound)

82.780

Moderate

0.72

rh-clint

Rat hepatocyte intrinsic clearance

1.014

uL/min/10^6 cells

Moderate

0.72

rh-fuinc

Rat hepatocyte fraction unbound in incubation

72.960

Moderate

0.72

rppb

Rat plasma protein binding (% unbound)

81.880

Moderate

0.72

solubility-dd

Solubility at pH 7.4 in DMSO

818.465

Moderate

0.72

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Gastric pH increased	56.25	38.01	6	317	47	90628077

MedDRA adverse event term

Likelihood ratio

Likelihood ratio threshold

Patients taking drug having adverse event

Patients taking drug not having adverse event

Patients not taking drug having adverse event

Patients not taking drug not having adverse event

Gastric pH increased

56.25

38.01

317

90628077

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Serotonin syndrome	165.88	95.08	35	169	25810	42595321

MedDRA adverse event term

Likelihood ratio

Likelihood ratio threshold

Patients taking drug having adverse event

Patients taking drug not having adverse event

Patients not taking drug having adverse event

Patients not taking drug not having adverse event

Serotonin syndrome

165.88

95.08

169

25810

42595321

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Serotonin syndrome	141.77	41.52	36	468	59117	110529678
Gastric pH increased	53.00	41.52	6	498	65	110588730
Drug interaction	42.64	41.52	27	477	500156	110088639

MedDRA adverse event term

Likelihood ratio

Likelihood ratio threshold

Patients taking drug having adverse event

Patients taking drug not having adverse event

Patients not taking drug having adverse event

Patients not taking drug not having adverse event

Serotonin syndrome

141.77

41.52

468

59117

110529678

Gastric pH increased

53.00

41.52

498

110588730

Drug interaction

42.64

41.52

477

500156

110088639

Pharmacologic Action:

Source	Code	Description
ATC	N06AX01	NERVOUS SYSTEM PSYCHOANALEPTICS ANTIDEPRESSANTS Other antidepressants
MeSH PA	D000928	Antidepressive Agents
MeSH PA	D011619	Psychotropic Drugs
MeSH PA	D018687	Antidepressive Agents, Second-Generation
CHEBI has role	CHEBI:25512	neurotransmitter
CHEBI has role	CHEBI:77746	human metabolite

Source

Code

Description

ATC

N06AX01

NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Other antidepressants

MeSH PA

D000928

Antidepressive Agents

MeSH PA

D011619

Psychotropic Drugs

MeSH PA

D018687

Antidepressive Agents, Second-Generation

CHEBI has role

CHEBI:25512

neurotransmitter

CHEBI has role

CHEBI:77746

human metabolite

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	2.23	acidic
pKa2	10.82	acidic
pKa3	13.4	acidic
pKa4	9.51	Basic

Dissociation level

Dissociation constant

Type (acidic/basic)

pKa1

2.23

acidic

pKa2

10.82

acidic

pKa3

13.4

acidic

pKa4

9.51

Basic

Bioactivity Summary:

Target	Class	Pharos	UniProt	Type	Activity value (-log[M])	Bioact source
5-hydroxytryptamine receptor 1A	GPCR	P08908	5HT1A_HUMAN	Ki	9.04	CHEMBL
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN	EC50	6.89	CHEMBL
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN	EC50	9	CHEMBL
5-hydroxytryptamine receptor 2C	GPCR	P28335	5HT2C_HUMAN	EC50	9.74	CHEMBL
5-hydroxytryptamine receptor 7	GPCR	P34969	5HT7R_HUMAN	Ki	8.67	CHEMBL

Target

Class

Pharos

UniProt

Action

Type

Activity value
(-log[M])

Mechanism
action

Bioact source

MoA source

5-hydroxytryptamine receptor 1A

GPCR

P08908

5HT1A_HUMAN

9.04

CHEMBL

5-hydroxytryptamine receptor 2A

GPCR

P28223

5HT2A_HUMAN

EC50

6.89

CHEMBL

5-hydroxytryptamine receptor 2B

GPCR

P41595

5HT2B_HUMAN

EC50

CHEMBL

5-hydroxytryptamine receptor 2C

GPCR

P28335

5HT2C_HUMAN

EC50

9.74

CHEMBL

5-hydroxytryptamine receptor 7

GPCR

P34969

5HT7R_HUMAN

8.67

CHEMBL

External reference:

ID	Source
4025452	VUID
N0000176007	NUI
D07339	KEGG_DRUG
4025452	VANDF
C0000578	UMLSCUI
CHEBI:17780	CHEBI
4PQ	PDB_CHEM_ID
CHEMBL350221	ChEMBL_ID
DB02959	DRUGBANK_ID
439280	PUBCHEM_CID
4407	INN_ID
C1LJO185Q9	UNII
94	RXNORM
17813	MMSL
59346	MMSL
d04726	MMSL
005314	NDDF
008831	NDDF
73916008	SNOMEDCT_US
D006916	MESH_DESCRIPTOR_UI
C1LJO185Q9	INXIGHT DRUGS

Source

4025452

VUID

N0000176007

NUI

D07339

KEGG_DRUG

4025452

VANDF

C0000578

UMLSCUI

CHEBI:17780