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

Stem definitionDrug idCAS RN
prostaglandins 4123 333963-40-9

Description:

MoleculeDescription

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: 3.83
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 2
  • TPSA: 83.83
  • ALOGS: -4.18
  • ROTB: 11

  • Status: ONP

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

Drug dosage:

None

ADMET properties:

PropertyValueReference
BA (Bioavailability) 0 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Jan. 31, 2006 FDA SUCAMPO PHARMA LLC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Dyspnoea 617.50 36.54 179 372 78554 2278980
Chest discomfort 239.72 36.54 61 490 14534 2343000
Nausea 167.30 36.54 77 474 112112 2245422
Diarrhoea 122.48 36.54 57 494 83507 2274027
Chest pain 83.85 36.54 32 519 28105 2329429
Dizziness 64.17 36.54 33 518 58632 2298902
Vomiting 63.48 36.54 35 516 71567 2285967
Syncope 60.38 36.54 22 529 16853 2340681
Constipation 55.06 36.54 22 529 21607 2335927
Colitis ischaemic 53.31 36.54 12 539 1625 2355909
Hypokalaemia 46.04 36.54 16 535 10638 2346896
Dehydration 40.97 36.54 18 533 22277 2335257
Palpitations 39.26 36.54 16 535 16440 2341094
Abdominal distension 38.75 36.54 14 537 10397 2347137
Completed suicide 38.70 36.54 17 534 21017 2336517

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Diarrhoea 58.41 39.67 26 189 53826 1692740
Nausea 40.60 39.67 20 195 51176 1695390

Pharmacologic Action:

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

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
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

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.76 acidic
pKa2 12.62 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
24MCG AMITIZA SUCAMPO PHARMA LLC N021908 Jan. 31, 2006 RX CAPSULE ORAL 6414016 Sept. 5, 2020 METHOD OF RELIEVING OR PREVENTING CONSTIPATION IN A HUMAN CONSTIPATED PATIENT
24MCG AMITIZA SUCAMPO PHARMA LLC N021908 Jan. 31, 2006 RX CAPSULE ORAL 6414016 Sept. 5, 2020 METHOD OF RELIEVING OR PREVENTING CONSTIPATION IN A HUMAN PATIENT WITH OPIOID-INDUCED CONSTIPATION
24MCG AMITIZA SUCAMPO PHARMA LLC N021908 Jan. 31, 2006 RX CAPSULE ORAL 8071613 Sept. 5, 2020 METHOD FOR RELIEVING OR TREATING CONSTIPATION IN A HUMAN CONSTIPATED PATIENT
24MCG AMITIZA SUCAMPO PHARMA LLC N021908 Jan. 31, 2006 RX CAPSULE ORAL 8071613 Sept. 5, 2020 METHOD FOR RELIEVING OR TREATING CONSTIPATION IN A PATIENT WITH OPIOID-INDUCED CONSTIPATION
8MCG AMITIZA SUCAMPO PHARMA LLC N021908 April 29, 2008 RX CAPSULE ORAL 6414016 Sept. 5, 2020 METHOD OF TREATING CONSTIPATION IN A PATIENT WITH IRRITABLE BOWEL SYNDROME
8MCG AMITIZA SUCAMPO PHARMA LLC N021908 April 29, 2008 RX CAPSULE ORAL 8071613 Sept. 5, 2020 METHOD FOR RELIEVING OR TREATING CONSTIPATION IN A PATIENT WITH IRRITABLE BOWEL SYNDROME
24MCG AMITIZA SUCAMPO PHARMA LLC N021908 Jan. 31, 2006 RX CAPSULE ORAL 7064148 Aug. 30, 2022 METHOD FOR TREATING CONSTIPATION BY OPENING CIC CHANNELS IN A MAMMALIAN SUBJECT
24MCG AMITIZA SUCAMPO PHARMA LLC N021908 Jan. 31, 2006 RX CAPSULE ORAL 7064148 Aug. 30, 2022 METHOD FOR TREATING CONSTIPATION IN A PATIENT WITH OPIOID-INDUCED CONSTIPATION BY OPENING CIC CHANNELS
8MCG AMITIZA SUCAMPO PHARMA LLC N021908 April 29, 2008 RX CAPSULE ORAL 7064148 Aug. 30, 2022 METHOD FOR TREATING CONSTIPATION BY OPENING CIC CHANNELS IN A MAMMALIAN SUBJECT
8MCG AMITIZA SUCAMPO PHARMA LLC N021908 April 29, 2008 RX CAPSULE ORAL 7064148 Aug. 30, 2022 METHOD OF TREATING CONSTIPATION IN A PATIENT WITH IRRITABLE BOWEL SYNDROME BY OPENING CHLORIDE CHANNELS (CIC)
24MCG AMITIZA SUCAMPO PHARMA LLC N021908 Jan. 31, 2006 RX CAPSULE ORAL 8097653 Nov. 14, 2022 METHOD FOR RELIEVING CONSTIPATION IN A HUMAN PATIENT THAT COMPRISES ADMINISTERING TO THE PATIENT A DOSAGE UNIT COMPRISING (I) 24MCG+/- 10% OF A DRUG SUBSTANCE AND (II) A PHARMACEUTICALLY SUITABLE EXCIPIENT
24MCG AMITIZA SUCAMPO PHARMA LLC N021908 Jan. 31, 2006 RX CAPSULE ORAL 8097653 Nov. 14, 2022 METHOD FOR RELIEVING CONSTIPATION IN A PATIENT WITH OPIOID-INDUCED CONSTIPATION THAT COMPRISES ADMINISTERING TO THE PATIENT A DOSAGE UNIT COMPRISING(I)24MICROG+/- 10% OF A DRUG SUBSTANCE AND (II) A PHARMACEUTICALLY SUITABLE EXCIPIENT
24MCG AMITIZA SUCAMPO PHARMA LLC N021908 Jan. 31, 2006 RX CAPSULE ORAL 8389542 Nov. 14, 2022 USE IN RELIEVING OR PREVENTING CONSTIPATION IN A HUMAN PATIENT WITH A DOSAGE UNIT COMPRISING 24MICROG+/- 10% OF A DRUG SUBSTANCE AND A PHARMACEUTICALLY SUITABLE EXCIPIENT
24MCG AMITIZA SUCAMPO PHARMA LLC N021908 Jan. 31, 2006 RX CAPSULE ORAL 8389542 Nov. 14, 2022 USE IN RELIEVING OR PREVENTING CONSTIPATION IN A PATIENT WITH OPIOID-INDUCED CONSTIPATION WITH A DOSAGE UNIT COMPRISING 24MICROG +/- 10% OF A DRUG SUBSTANCE AND A PHARMACEUTICALLY SUITABLE EXCIPIENT
24MCG AMITIZA SUCAMPO PHARMA LLC N021908 Jan. 31, 2006 RX CAPSULE ORAL 6982283 Dec. 4, 2022 METHOD FOR TREATING OPIOID-INDUCED CONSTIPATION
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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
24MCG AMITIZA SUCAMPO PHARMA LLC N021908 Jan. 31, 2006 RX CAPSULE ORAL April 26, 2021 REVISIONS TO SECTION 8.4 OF THE PRESCRIBING INFORMATION TO INCLUDE A SAFETY AND EFFICACY STUDY IN PEDIATRIC PATIENTS AGES >=6 YEARS TO <18 YEARS WITH CHRONIC IDIOPATHIC CONSTIPATION
8MCG AMITIZA SUCAMPO PHARMA LLC N021908 April 29, 2008 RX CAPSULE ORAL April 26, 2021 REVISIONS TO SECTION 8.4 OF THE PRESCRIBING INFORMATION TO INCLUDE A SAFETY AND EFFICACY STUDY IN PEDIATRIC PATIENTS AGES >=6 YEARS TO <18 YEARS WITH CHRONIC IDIOPATHIC CONSTIPATION

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Chloride channel protein 2 Ion channel OPENER DRUGBANK CHEMBL

External reference:

IDSource
D000068238 MESH_DESCRIPTOR_UI
4025090 VUID
N0000175352 NUI
C1684405 UMLSCUI
D04790 KEGG_DRUG
7662KG2R6K UNII
8254 INN_ID
136790-76-6 SECONDARY_CAS_RN
420304008 SNOMEDCT_US
21067 MMSL
d05736 MMSL
623033 RXNORM
421856003 SNOMEDCT_US
4025090 VANDF
011200 NDDF
DB01046 DRUGBANK_ID
CHEBI:34945 CHEBI
CHEMBL1201134 ChEMBL_ID
157920 PUBCHEM_CID
4242 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
AMITIZA HUMAN PRESCRIPTION DRUG LABEL 1 16590-622 CAPSULE, GELATIN COATED 8 ug ORAL NDA 16 sections
Amitiza HUMAN PRESCRIPTION DRUG LABEL 1 35356-500 CAPSULE, GELATIN COATED 24 ug ORAL NDA 16 sections
Amitiza HUMAN PRESCRIPTION DRUG LABEL 1 54868-5971 CAPSULE, GELATIN COATED 24 ug ORAL NDA 16 sections
Amitiza HUMAN PRESCRIPTION DRUG LABEL 1 54868-6153 CAPSULE, GELATIN COATED 8 ug ORAL NDA 16 sections
Amitiza HUMAN PRESCRIPTION DRUG LABEL 1 63629-6398 CAPSULE, GELATIN COATED 24 ug ORAL NDA 18 sections
Amitiza HUMAN PRESCRIPTION DRUG LABEL 1 64764-080 CAPSULE, GELATIN COATED 8 ug ORAL NDA 17 sections
Amitiza HUMAN PRESCRIPTION DRUG LABEL 1 64764-240 CAPSULE, GELATIN COATED 24 ug ORAL NDA 17 sections
Amitiza HUMAN PRESCRIPTION DRUG LABEL 1 68151-5003 CAPSULE, GELATIN COATED 24 ug ORAL NDA 17 sections