Details of the Drug

General Information of Drug (ID: DMRJSP8)

Drug Name

Orlistat

Synonyms

orlistat; 96829-58-2; Tetrahydrolipstatin; Xenical; Alli; Orlipastat; (-)-Tetrahydrolipstatin; Orlipastatum; Orlipastatum [INN-Latin]; THLP; Ro-18-0647; UNII-95M8R751W8; C29H53NO5; Ro 18-0647/002; N-Formyl-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester; (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate; Orlistat (Alli, Xenical); MLS002207022; [(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2S)-2-formamido-4-methylpentanoate; CHEMBL175247; Alli; GlaxoSmithKline brand of orlistat; Roche brand of orlistat; Alli (TN); Hoffmann-La Roche brand of orlistat; KS-1183; Orlistat [USAN:INN]; R-212; Xenical (TN); Orlistat (USAN/INN); Ro 18-0647/008; Alli, Xenical, Tetrahydrolipstatin, Orlistat; N-Formyl-L-leucine, ester with (3S,4S)-3-hexyl-4-((2S)-2-hydroxytridecyl)-2-oxetanone; L-Leucine, N-formyl-, (1S)-1-(((2S,3S)-3-hexyl-4-oxo-2-oxetanyl)methyl)dodecyl ester; L-Leucine,N-formyl-, (1S)-1-(((2S,3S)-3-hexyl-4-oxo-2-oxetanyl)methyl)dodecyl ester; 1-((3-hexyl-4-oxo-2-oxetanyl)methyl)dodecyl-2-formamido-4-methylvalerate; TETRAHYDROLIPSTATIN

Indication

Disease Entry	ICD 11	Status	REF
Obesity	5B81	Approved	[1], [2], [3], [4]

Therapeutic Class

Antiobesity Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

495.7

Topological Polar Surface Area (xlogp)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [5]
Elimination: After single oral dose of radiolabled orlistat in both normal weight and obese volunteers fecal excretion of the unabsorbed drug was found to be the major route of elimination with <2% urinary excretion [6]
Half-life: The concentration or amount of drug in body reduced by one-half in 1 - 2 hours [7]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 9.221 micromolar/kg/day [8]

Chemical Identifiers

Formula: C29H53NO5
IUPAC Name: [(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2S)-2-formamido-4-methylpentanoate
Canonical SMILES: CCCCCCCCCCC[C@@H](C[C@H]1[C@@H](C(=O)O1)CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
InChI: InChI=1S/C29H53NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h22-27H,5-21H2,1-4H3,(H,30,31)/t24-,25-,26-,27-/m0/s1
InChIKey: AHLBNYSZXLDEJQ-FWEHEUNISA-N

Cross-matching ID

PubChem CID: 3034010
ChEBI ID: CHEBI:94686
CAS Number: 96829-58-2
DrugBank ID: DB01083
TTD ID: D0T9TJ
ACDINA ID: D00491

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Cannabinoid receptor 1 (CB1)	TT6OEDT	CNR1_HUMAN	Inhibitor	[9]
Pancreatic triacylglycerol lipase (PNLIP)	TTXMY0J	LIPP_HUMAN	Modulator	[10]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Obesity

ICD Disease Classification

5B81

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Cannabinoid receptor 1 (CB1)	DTT	CNR1	5.59E-02	-0.22	-0.45
Cannabinoid receptor 1 (CB1)	DTT	CNR1	7.68E-01	-0.06	-0.46

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Orlistat (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Orlistat and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[29]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Orlistat and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[30]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Orlistat and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[31]
Doxercalciferol	DM6FG1P	Minor	Decreased absorption of Orlistat caused by Doxercalciferol.	Chronic kidney disease [GB61]	[32]
Anisindione	DM2C48U	Moderate	Altered absorption of Orlistat caused by Anisindione.	Coagulation defect [3B10]	[33]
Ospemifene	DMC4GEI	Moderate	Altered absorption of Orlistat caused by Ospemifene.	Dyspareunia [GA12]	[34]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Orlistat and Cannabidiol.	Epileptic encephalopathy [8A62]	[34]
Boceprevir	DMBSHMF	Moderate	Altered absorption of Orlistat caused by Boceprevir.	Hepatitis virus infection [1E50-1E51]	[35]
Telaprevir	DMMRV29	Moderate	Altered absorption of Orlistat caused by Telaprevir.	Hepatitis virus infection [1E50-1E51]	[35]
Telbivudine	DMSWUGE	Moderate	Altered absorption of Orlistat caused by Telbivudine.	Hepatitis virus infection [1E50-1E51]	[35]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Orlistat and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[36]
Fosamprenavir	DM4W9B3	Moderate	Altered absorption of Orlistat caused by Fosamprenavir.	Human immunodeficiency virus disease [1C60-1C62]	[35]
Dolutegravir	DMCZGRE	Moderate	Altered absorption of Orlistat caused by Dolutegravir.	Human immunodeficiency virus disease [1C60-1C62]	[35]
Saquinavir	DMG814N	Moderate	Altered absorption of Orlistat caused by Saquinavir.	Human immunodeficiency virus disease [1C60-1C62]	[35]
Elvitegravir	DMG9B1U	Moderate	Altered absorption of Orlistat caused by Elvitegravir.	Human immunodeficiency virus disease [1C60-1C62]	[35]
Rilpivirine	DMJ0QOW	Moderate	Altered absorption of Orlistat caused by Rilpivirine.	Human immunodeficiency virus disease [1C60-1C62]	[35]
Darunavir	DMN3GCH	Moderate	Altered absorption of Orlistat caused by Darunavir.	Human immunodeficiency virus disease [1C60-1C62]	[35]
Raltegravir	DMYURI6	Moderate	Altered absorption of Orlistat caused by Raltegravir.	Human immunodeficiency virus disease [1C60-1C62]	[35]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Orlistat and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[37]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Orlistat and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[38]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Orlistat and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[39]
Glycerol phenylbutyrate	DMDGRQO	Moderate	Altered absorption of Orlistat caused by Glycerol phenylbutyrate.	Liver disease [DB90-DB9Z]	[34]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Orlistat and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[40]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Orlistat and Idelalisib.	Mature B-cell leukaemia [2A82]	[41]
Leflunomide	DMR8ONJ	Major	Increased risk of hepatotoxicity by the combination of Orlistat and Leflunomide.	Rheumatoid arthritis [FA20]	[38]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Orlistat and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[34]
Amiodarone	DMUTEX3	Moderate	Decreased absorption of Orlistat caused by Amiodarone.	Ventricular tachyarrhythmia [BC71]	[32]
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⏷ Show the Full List of 27 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Ammonia	E00007	222	Alkalizing agent
Butyl alcohol	E00011	263	Flavoring agent; Solvent
Ferrosoferric oxide	E00231	14789	Colorant
Ferrous oxide	E00241	14945	Colorant
Potassium hydroxide	E00233	14797	Alkalizing agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
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⏷ Show the Full List of 12 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Orlistat 120 mg capsule	120 mg	Oral Capsule	Oral
Orlistat 60 mg capsule	60 mg	Oral Capsule	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

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