Oxitriptan

Summary

Oxitriptan (CHEMBL350221) is an approved small molecule (ATC N06AX01) targeting SLC36A1 and SLC36A2; indicated across 4 conditions including depressive disorder and sleep disorder.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: N06AX01
• Targets: 2 (SLC36A1, SLC36A2)
• Indications: 4 conditions
• Clinical trials: 8
• Chemistry: 220.22 Da · C11H12N2O3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL350221
Name	Oxitriptan
Type	Small molecule
Max phase	3
FDA approved	yes
PubChem CID	439280
ChEBI	CHEBI:17780
ATC	N06AX01
Molecular formula	C11H12N2O3
Molecular weight	220.22
InChIKey	LDCYZAJDBXYCGN-VIFPVBQESA-N

SMILES: C1=CC2=C(C=C1O)C(=CN2)C[C@@H](C(=O)O)N

IUPAC name: (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid

ChEBI definition: The L-enantiomer of 5-hydroxytryptophan.

Other ChEBI roles (chemical / environmental): human metabolite, plant metabolite, mouse metabolite.

Also known as: dl-, Cincofarm, Dl-hydroxytryptophan, Dl-oxitriptan, Hydroxytryptophan, Levothym, Levotinine, Levotonine, NSC-92523, Oxitriptan, Oxyfan, Pretonine

Patent coverage: 4,587 distinct patent families (14,247 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 14,220 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
SLC36A1	Proton-coupled Amino acid Transporter 1	Inhibition	3	0.2%	Q7Z2H8
SLC36A2	Proton-coupled Amino acid Transporter 2	Inhibition	2.8	0%	Q495M3

Broader ChEMBL bioactivity targets: 27 (assay-derived). Sample: Microtubule-associated protein tau, Lysine-specific demethylase 4E, Nuclear receptor ROR-gamma, Fructose-bisphosphate aldolase, Prelamin-A/C, RecQ-like DNA helicase BLM, Peripheral myelin protein 22, Histone-lysine N-methyltransferase 2A, 5-hydroxytryptamine receptor 2B, Thyrotropin receptor.

Bioactivity

ChEMBL activities: 22 potent at pChembl ≥ 5 of 44 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
HTR2C	9.74	EC50	0.18	nM	CHEMBL_ACT_16482509
HTR2C	9.66	EC50	0.22	nM	CHEMBL_ACT_16482508
HTR1A	9.04	Ki	0.91	nM	CHEMBL_ACT_15180259
HTR2B	9	EC50	1	nM	CHEMBL_ACT_16482511
HTR2B	8.89	EC50	1.29	nM	CHEMBL_ACT_16482510
HTR2A	8.87	EC50	1.35	nM	CHEMBL_ACT_16482512
HTR1A	8.74	Ki	1.8	nM	CHEMBL_ACT_15697708
HTR2A	8.72	EC50	1.9	nM	CHEMBL_ACT_16482513
HTR7	8.67	Ki	2.12	nM	CHEMBL_ACT_15180286
Q62758	8.01	EC50	9.77	nM	CHEMBL_ACT_530565
LMNA	7.4	Potency	39.8	nM	CHEMBL_ACT_3645486
HTR2A	6.89	EC50	130	nM	CHEMBL_ACT_15697686
P35563	6.8	Ki	158.5	nM	CHEMBL_ACT_530567
ADORA3	6.12	AC50	765	nM	CHEMBL_ACT_25198808
NPSR1	5.4	Potency	3981	nM	CHEMBL_ACT_4900708
P08482	5.35	Potency	4467	nM	CHEMBL_ACT_4811353
TSHR	5.3	Potency	5012	nM	CHEMBL_ACT_3941176
A8B2U2	5.3	Potency	5000	nM	CHEMBL_ACT_4609902
TSHR	5.3	Potency	5012	nM	CHEMBL_ACT_4751361
HTR1A	5.19	AC50	6469	nM	CHEMBL_ACT_25165131
P00811	5.15	Potency	7080	nM	CHEMBL_ACT_4642504
HTR2B	5	AC50	10080	nM	CHEMBL_ACT_25201572

Target pathways

Aggregated over 2 target gene(s): SLC36A1, SLC36A2.

Top Reactome pathways

9 total, by targets touching each:

Pathway	Targets	Genes
Amino acid transport across the plasma membrane	2	SLC36A1, SLC36A2
Transport of small molecules	2	SLC36A1, SLC36A2
R-HSA-425393	2	SLC36A1, SLC36A2
SLC-mediated transmembrane transport	2	SLC36A1, SLC36A2
Proton-coupled neutral amino acid transporters	2	SLC36A1, SLC36A2
Disease	1	SLC36A2
Defective SLC36A2 causes iminoglycinuria (IG) and hyperglycinuria (HG)	1	SLC36A2
SLC transporter disorders	1	SLC36A2
Disorders of transmembrane transporters	1	SLC36A2

Dominant GO biological processes

GO term	Targets
monoatomic ion transport	2
amino acid transport	2
L-alanine transport	2
glycine transport	2
proline transport	2
proline transmembrane transport	2
proton transmembrane transport	2
taurine transmembrane transport	1
alanine transport	1
amino acid import across plasma membrane	1
neutral amino acid transport	1

Indications & clinical

Indications

4 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
depressive disorder	4	MONDO:0002050	MONDO:0002009
sleep disorder	3	MONDO:0100081	EFO:0008568
spinal cord injury	2	MONDO:0043797	EFO:1001919
obesity disorder	2	MONDO:0011122	EFO:0001073

Clinical trials

Total trials: 8.

Phase distribution

Phase	Trials
PHASE2	3
PHASE4	2
Not specified	2
PHASE2/PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT02356107	PHASE4	COMPLETED	5-hydroxytryptophan and Creatine for Treatment Resistant Depression Associated With Hypoxia in Females
NCT02922725	PHASE4	TERMINATED	Placebo-controlled Trial of 5-hydroxytryptophan and Creatine for SSRI or SNRI Augmentation in Treatment Resistant Depression in Females
NCT04520178	PHASE2/PHASE3	RECRUITING	Effects of 5HTP on the Injured Human Spinal Cord
NCT04160910	PHASE2	RECRUITING	5HTP Regulation Of Asthma In Children
NCT04395183	PHASE2	COMPLETED	5-HTP and Creatine for Depression
NCT05030129	PHASE2	COMPLETED	ERG/5-HTP in Fragile X Syndrome (FXS)
NCT00731003	Not specified	COMPLETED	The Effect of Serotonergic Modulation on Intestinal Permeability and Visceral Hypersensitivity in Healthy Individuals and Irritable Bowel Syndrome (IBS) Patients
NCT01514409	Not specified	COMPLETED	Sub-chronic Effects of 5-hydroxytryptophan on Mood and Emotional Processing in Healthy Volunteers

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

10 molecules share ≥1 primary target. Top 10 by shared-target count:

Molecule	Source	Status	Shared targets
.gamma.-aminobutyric acid	PubChem	Approved	SLC36A1
aminocaproic acid	PubChem	Approved	SLC36A1
Creatinine	PubChem	Approved	SLC36A1
Cycloserine	PubChem	Approved	SLC36A1
cysteine	PubChem	Approved	SLC36A1
Glycine	PubChem	Approved	SLC36A1
hydroxyproline	PubChem	Approved	SLC36A1
leucine	PubChem	Approved	SLC36A1
oxybate	PubChem	Approved	SLC36A1
Taurine	PubChem	Approved	SLC36A1