lubiprostone 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
prostaglandins	4123	333963-40-9

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: lubiprostone amitiza	Member of a bicyclic fatty acid class of compounds derived from PROSTAGLANDIN E1 involved in chloride channel gating. Molecular weight: 390.47 Formula: C20H32F2O5 CLOGP: 3.47 LIPINSKI: 0 HAC: 5 HDO: 2 TPSA: 83.83 ALOGS: -4.18 ROTB: 11 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

lubiprostone
amitiza

Member of a bicyclic fatty acid class of compounds derived from PROSTAGLANDIN E1 involved in chloride channel gating.

Molecular weight: 390.47
Formula: C20H32F2O5
CLOGP: 3.47
LIPINSKI: 0
HAC: 5
HDO: 2
TPSA: 83.83
ALOGS: -4.18
ROTB: 11

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

None

ADMET properties:

Property	Value	Reference
BA (Bioavailability)	0 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Bocci G, Oprea TI, Benet LZ

Approvals:

Date	Agency	Company	Orphan
Jan. 31, 2006	FDA	SUCAMPO PHARMA LLC

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
Dyspnoea	81.70	13.74	240	8692	661073	62819017
Chest discomfort	65.51	13.74	79	8853	109890	63370200
Urine chloride decreased	43.17	13.74	8	8924	87	63480003
Urine sodium decreased	38.48	13.74	8	8924	163	63479927
Constipation	31.79	13.74	86	8846	224857	63255233
Drug intolerance	25.63	13.74	6	8926	308655	63171435
Nausea	22.39	13.74	200	8732	854271	62625819
Ileus	20.87	13.74	17	8915	14708	63465382
Contraindicated product administered	20.69	13.74	3	8929	217645	63262445
Rheumatoid arthritis	19.06	13.74	6	8926	253813	63226277
Metabolic alkalosis	18.79	13.74	9	8923	3052	63477038
Abdominal distension	17.44	13.74	38	8894	86577	63393513
Subacute hepatic failure	17.33	13.74	4	8928	134	63479956
Impaired gastric emptying	16.94	13.74	13	8919	10319	63469771
Infusion related reaction	16.41	13.74	7	8925	245514	63234576
Anxiety	16.18	13.74	67	8865	217474	63262616
Glossodynia	15.81	13.74	3	8929	178873	63301217
Depression	15.79	13.74	62	8870	196430	63283660
Loss of consciousness	15.50	13.74	44	8888	118077	63362013
Feeling abnormal	15.48	13.74	51	8881	148341	63331749
Chest pain	14.88	13.74	65	8867	215894	63264196
Altered state of consciousness	14.79	13.74	18	8914	25212	63454878
Cholecystitis chronic	14.76	13.74	12	8920	10349	63469741
Colitis ischaemic	14.41	13.74	12	8920	10696	63469394
Hepatobiliary scan abnormal	14.39	13.74	3	8929	62	63480028
Syncope	13.76	13.74	42	8890	117343	63362747

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
Hepatic function abnormal	48.05	18.91	38	3475	44325	34909093
Toxic optic neuropathy	42.54	18.91	11	3502	839	34952579
Pneumonia aspiration	35.20	18.91	31	3482	41872	34911546
Decreased appetite	31.10	18.91	58	3455	166334	34787084
Interstitial lung disease	23.79	18.91	31	3482	65251	34888167
Ileus	21.96	18.91	16	3497	16483	34936935

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
Hepatic function abnormal	48.42	14.53	53	10141	73054	79661140
Chest discomfort	42.86	14.53	69	10125	137975	79596219
Urine chloride decreased	42.84	14.53	8	10186	101	79734093
Toxic optic neuropathy	40.95	14.53	12	10182	1141	79733053
Dyspnoea	40.06	14.53	215	9979	856810	78877384
Urine sodium decreased	35.09	14.53	8	10186	280	79733914
Decreased appetite	34.43	14.53	109	10085	342309	79391885
Ileus	32.72	14.53	27	10167	26184	79708010
Altered state of consciousness	29.40	14.53	32	10162	43790	79690404
Pneumonia aspiration	25.76	14.53	37	10157	66930	79667264
Hypokalaemia	24.77	14.53	56	10138	143984	79590210
Toxicity to various agents	23.95	14.53	12	10182	421528	79312666
Drug intolerance	23.55	14.53	3	10191	264116	79470078
Nausea	22.97	14.53	204	9990	956992	78777202
Metabolic alkalosis	22.07	14.53	11	10183	4478	79729716
Interstitial lung disease	21.89	14.53	46	10148	112554	79621640
Constipation	21.37	14.53	82	10112	282968	79451226
Immobilisation syndrome	20.88	14.53	6	10188	532	79733662
Abdominal distension	17.83	14.53	44	10150	119606	79614588
Diarrhoea	17.77	14.53	181	10013	880308	78853886
Blood pressure decreased	16.35	14.53	38	10156	99428	79634766
Enterocolitis	16.16	14.53	14	10180	14498	79719696
Colon cancer	16.15	14.53	14	10180	14509	79719685
Loss of consciousness	15.52	14.53	52	10142	167891	79566303
Colitis ischaemic	15.47	14.53	14	10180	15345	79718849
Stoma site pain	15.02	14.53	6	10188	1452	79732742

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	A06AX03	ALIMENTARY TRACT AND METABOLISM DRUGS FOR CONSTIPATION DRUGS FOR CONSTIPATION Other drugs for constipation
FDA MoA	N0000175456	Chloride Channel Activators
FDA EPC	N0000175573	Chloride Channel Activator
MeSH PA	D065101	Chloride Channel Agonists
MeSH PA	D049990	Membrane Transport Modulators

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID
Chronic idiopathic constipation	indication	82934008
Irritable bowel syndrome characterized by constipation	indication	440630006
Gastrointestinal obstruction	contraindication	126765001
Pregnancy, function	contraindication	289908002
Severe diarrhea	contraindication	409587002

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	4.76	acidic
pKa2	12.62	acidic

Orange Book patent data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
8MCG	AMITIZA	SUCAMPO PHARMA LLC	N021908	April 29, 2008	RX	CAPSULE	ORAL	7795312	Sept. 17, 2024	METHOD FOR TREATING IRRITABLE BOWEL SYNDROME AND METHOD FOR TREATING ABDOMINAL DISCOMFORT ASSOCIATED WITH IRRITABLE BOWEL SYNDROME
24MCG	AMITIZA	SUCAMPO PHARMA LLC	N021908	Jan. 31, 2006	RX	CAPSULE	ORAL	8748481	Sept. 1, 2025	METHOD FOR THE LONG TERM TREATMENT OF CHRONIC CONSTIPATION IN A HUMAN SUBJECT
8MCG	AMITIZA	SUCAMPO PHARMA LLC	N021908	April 29, 2008	RX	CAPSULE	ORAL	8748481	Sept. 1, 2025	METHOD FOR THE LONG TERM TREATMENT OF CHRONIC CONSTIPATION IN A HUMAN SUBJECT WITH IRRITABLE BOWEL SYNDROME

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Chloride channel protein 2	Ion channel	P51788	CLCN2_HUMAN	OPENER				DRUGBANK	CHEMBL

External reference:

ID	Source
4025090	VUID
N0000175352	NUI
D04790	KEGG_DRUG
4025090	VANDF
C1684405	UMLSCUI
CHEBI:34945	CHEBI
CHEMBL1201134	ChEMBL_ID
D000068238	MESH_DESCRIPTOR_UI
DB01046	DRUGBANK_ID
4242	IUPHAR_LIGAND_ID
8254	INN_ID
7662KG2R6K	UNII
157920	PUBCHEM_CID
615205	RXNORM
21067	MMSL
342325	MMSL
76092	MMSL
d05736	MMSL
011200	NDDF
420304008	SNOMEDCT_US
421856003	SNOMEDCT_US
136790-76-6	SECONDARY_CAS_RN

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	0254-3028	CAPSULE, GELATIN COATED	8 ug	ORAL	NDA AUTHORIZED GENERIC	29 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	0254-3029	CAPSULE, GELATIN COATED	24 ug	ORAL	NDA AUTHORIZED GENERIC	29 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	0480-3479	CAPSULE, GELATIN COATED	8 ug	ORAL	ANDA	26 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	0480-4138	CAPSULE, GELATIN COATED	24 ug	ORAL	ANDA	26 sections
AMITIZA	HUMAN PRESCRIPTION DRUG LABEL	1	16590-622	CAPSULE, GELATIN COATED	8 ug	ORAL	NDA	26 sections
Amitiza	HUMAN PRESCRIPTION DRUG LABEL	1	35356-500	CAPSULE, GELATIN COATED	24 ug	ORAL	NDA	28 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	42291-475	CAPSULE	8 ug	ORAL	ANDA	25 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	42291-476	CAPSULE	24 ug	ORAL	ANDA	25 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	43598-163	CAPSULE, GELATIN COATED	8 ug	ORAL	NDA AUTHORIZED GENERIC	29 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	43598-168	CAPSULE, GELATIN COATED	24 ug	ORAL	NDA AUTHORIZED GENERIC	29 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	51407-744	CAPSULE, GELATIN COATED	8 ug	ORAL	NDA authorized generic	28 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	51407-745	CAPSULE, GELATIN COATED	24 ug	ORAL	NDA authorized generic	28 sections
Amitiza	HUMAN PRESCRIPTION DRUG LABEL	1	54868-5971	CAPSULE, GELATIN COATED	24 ug	ORAL	NDA	25 sections
Amitiza	HUMAN PRESCRIPTION DRUG LABEL	1	54868-6153	CAPSULE, GELATIN COATED	8 ug	ORAL	NDA	25 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	55700-963	CAPSULE, GELATIN COATED	24 ug	ORAL	NDA AUTHORIZED GENERIC	29 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	55700-963	CAPSULE, GELATIN COATED	24 ug	ORAL	NDA AUTHORIZED GENERIC	29 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	63304-351	CAPSULE, GELATIN COATED	8 ug	ORAL	NDA authorized generic	28 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	63304-352	CAPSULE, GELATIN COATED	24 ug	ORAL	NDA authorized generic	28 sections
Amitiza	HUMAN PRESCRIPTION DRUG LABEL	1	64764-080	CAPSULE, GELATIN COATED	8 ug	ORAL	NDA	27 sections
Amitiza	HUMAN PRESCRIPTION DRUG LABEL	1	64764-080	CAPSULE, GELATIN COATED	8 ug	ORAL	NDA	27 sections
Amitiza	HUMAN PRESCRIPTION DRUG LABEL	1	64764-240	CAPSULE, GELATIN COATED	24 ug	ORAL	NDA	27 sections
Amitiza	HUMAN PRESCRIPTION DRUG LABEL	1	64764-240	CAPSULE, GELATIN COATED	24 ug	ORAL	NDA	27 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	65162-841	CAPSULE	8 ug	ORAL	ANDA	25 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	65162-841	CAPSULE	8 ug	ORAL	ANDA	25 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	65162-841	CAPSULE	8 ug	ORAL	ANDA	25 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	65162-842	CAPSULE	24 ug	ORAL	ANDA	25 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	65162-842	CAPSULE	24 ug	ORAL	ANDA	25 sections
Lubiprostone	HUMAN PRESCRIPTION DRUG LABEL	1	65162-842	CAPSULE	24 ug	ORAL	ANDA	25 sections
Amitiza	HUMAN PRESCRIPTION DRUG LABEL	1	68151-5003	CAPSULE, GELATIN COATED	24 ug	ORAL	NDA	26 sections
LUBIPROSTONE	Human Prescription Drug Label	1	69339-162	CAPSULE	8 ug	ORAL	NDA	25 sections