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

Stem definitionDrug idCAS RN
histamine-H2-receptor antagonists, cimetidine derivatives 645 51481-61-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cimetidine
  • tagamet
  • tametin
  • ulcedin
  • ulcedine
  • ulcerex
  • ulcerfen
  • cimetidine hydrochloride
  • cimetidine HCl
A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.
  • Molecular weight: 252.34
  • Formula: C10H16N6S
  • CLOGP: 0.38
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 3
  • TPSA: 88.89
  • ALOGS: -3.16
  • ROTB: 5

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.80 g O
0.80 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 6.20 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 62 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 158.51 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 60 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.20 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 8.10 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.78 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Aug. 16, 1977 FDA

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
Urine abnormality 111.46 12.70 46 12925 5548 46667543
Urine leukocyte esterase positive 106.38 12.70 36 12935 2499 46670592
Body tinea 62.83 12.70 19 12952 916 46672175
Lymphocyte count decreased 60.66 12.70 53 12918 25536 46647555
Chronic kidney disease 53.00 12.70 61 12910 40810 46632281
Inhibitory drug interaction 48.72 12.70 19 12952 1976 46671115
Urine ketone body present 47.41 12.70 19 12952 2123 46670968
Infection susceptibility increased 47.10 12.70 19 12952 2160 46670931
Blood urine present 45.33 12.70 33 12938 12249 46660842
Culture urine positive 45.14 12.70 21 12950 3370 46669721
Anaphylactoid reaction 44.56 12.70 21 12950 3470 46669621
Rheumatoid arthritis 44.09 12.70 7 12964 240208 46432883
Impaired quality of life 42.92 12.70 20 12951 3222 46669869
Erythema 37.02 12.70 105 12866 142715 46530376
Glucose tolerance impaired 35.38 12.70 20 12951 4811 46668280
Torsade de pointes 34.63 12.70 28 12943 12126 46660965
Creatinine urine decreased 28.16 12.70 7 12964 160 46672931
Hyperlipidaemia 28.04 12.70 30 12941 18509 46654582
Hypertension 26.97 12.70 117 12854 196239 46476852
Product dose omission issue 26.58 12.70 7 12964 168513 46504578
Purpura 26.40 12.70 22 12949 9936 46663155
Neutrophil count increased 25.04 12.70 25 12946 14228 46658863
Bone density decreased 24.73 12.70 21 12950 9731 46663360
C-reactive protein abnormal 24.67 12.70 30 12941 21240 46651851
Electrocardiogram T wave amplitude decreased 22.98 12.70 7 12964 346 46672745
Keratitis 22.97 12.70 12 12959 2471 46670620
Drug ineffective 22.85 12.70 104 12867 677734 45995357
Infusion site scar 21.92 12.70 6 12965 202 46672889
Poor quality sleep 21.87 12.70 24 12947 15229 46657862
Urticaria 21.65 12.70 77 12894 117815 46555276
Drug intolerance 21.55 12.70 7 12964 147042 46526049
Tri-iodothyronine free decreased 21.19 12.70 6 12965 229 46672862
Death 20.37 12.70 161 12810 335387 46337704
Impaired work ability 20.09 12.70 21 12950 12615 46660476
Red blood cells urine positive 19.65 12.70 11 12960 2596 46670495
Circulatory collapse 19.60 12.70 27 12944 21597 46651494
Food interaction 19.54 12.70 7 12964 575 46672516
Chromaturia 18.76 12.70 22 12949 14997 46658094
Band sensation 18.46 12.70 7 12964 675 46672416
Red cell distribution width increased 18.33 12.70 16 12955 7688 46665403
Joint swelling 18.02 12.70 12 12959 166061 46507030
Palmar-plantar erythrodysaesthesia syndrome 17.74 12.70 25 12946 20426 46652665
Anxiety 16.85 12.70 97 12874 181860 46491231
Treatment failure 16.42 12.70 3 12968 93084 46580007
Thyroid cyst 16.00 12.70 6 12965 561 46672530
Pancreatitis acute 15.38 12.70 26 12945 24846 46648245
Feeling hot 15.23 12.70 33 12938 37895 46635196
Infusion site discomfort 15.07 12.70 6 12965 659 46672432
Glucose urine present 15.01 12.70 6 12965 666 46672425
Bacterial test positive 14.36 12.70 11 12960 4405 46668686
Oral herpes 14.35 12.70 22 12949 19368 46653723
Basophil count increased 13.76 12.70 6 12965 828 46672263
Specific gravity urine decreased 13.62 12.70 5 12966 440 46672651
Blood thyroid stimulating hormone increased 13.59 12.70 12 12959 5857 46667234
Secondary adrenocortical insufficiency 13.48 12.70 6 12965 869 46672222
Skin disorder 13.40 12.70 23 12948 22240 46650851
Alanine aminotransferase increased 13.12 12.70 54 12917 88397 46584694
Lactic acidosis 13.04 12.70 29 12942 33880 46639211
Leukocyturia 13.02 12.70 6 12965 942 46672149
Product use issue 13.01 12.70 5 12966 94639 46578452
Protein urine present 12.91 12.70 11 12960 5120 46667971
Infusion site rash 12.86 12.70 6 12965 969 46672122
pH urine increased 12.77 12.70 4 12967 217 46672874

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
Chronic kidney disease 32.44 15.31 37 5368 37801 29909272
Palmar-plantar erythrodysaesthesia syndrome 20.90 15.31 19 5386 14851 29932222
Peptic ulcer 17.53 15.31 9 5396 2759 29944314
Adulterated product 16.63 15.31 3 5402 21 29947052
Renal injury 16.51 15.31 15 5390 11714 29935359
Flushing 16.02 15.31 23 5382 29469 29917604

Pharmacologic Action:

SourceCodeDescription
ATC A02BA01 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR ACID RELATED DISORDERS
DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
H2-receptor antagonists
ATC A02BA51 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR ACID RELATED DISORDERS
DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
H2-receptor antagonists
FDA MoA N0000000151 Histamine H2 Receptor Antagonists
FDA EPC N0000175784 Histamine-2 Receptor Antagonist
CHEBI has role CHEBI:37961 h2-receptor blockers
CHEBI has role CHEBI:49201 anti-ulcer agents
CHEBI has role CHEBI:50183 cytochrome p450 inhibitor
CHEBI has role CHEBI:60809 adjuvants
MeSH PA D000897 Anti-Ulcer Agents
MeSH PA D065609 Cytochrome P-450 CYP1A2 Inhibitors
MeSH PA D065607 Cytochrome P-450 Enzyme Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D005765 Gastrointestinal Agents
MeSH PA D018494 Histamine Agents
MeSH PA D006633 Histamine Antagonists
MeSH PA D006635 Histamine H2 Antagonists
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D018377 Neurotransmitter Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Heartburn indication 16331000
Upper gastrointestinal hemorrhage indication 37372002
Duodenal ulcer disease indication 51868009 DOID:1724
Zollinger-Ellison syndrome indication 53132006 DOID:0050782
Multiple endocrine adenomas indication 60549007
Indigestion indication 162031009
Gastroesophageal reflux disease indication 235595009 DOID:8534
Systemic mast cell disease indication 397016004 DOID:349
Gastric ulcer indication 397825006 DOID:10808
Upper GI Bleed Prevention indication
Maintenance of Healing Duodenal Ulcer indication
Pancreatic insufficiency off-label use 37992001
Urticaria off-label use 126485001
Prevention of Stress Ulcer off-label use
NSAID-Induced Gastric Ulcer off-label use
Impaired renal function disorder contraindication 197663003
Disease of liver contraindication 235856003 DOID:409
Malignant tumor of stomach contraindication 363349007 DOID:10534

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.83 acidic
pKa2 6.71 Basic
pKa3 0.0 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Histamine H2 receptor GPCR ANTAGONIST Kd 6.14 WOMBAT-PK CHEMBL
Multidrug and toxin extrusion protein 1 Transporter IC50 5.92 CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 5.15 PDSP
Multidrug and toxin extrusion protein 2 Transporter INHIBITOR Ki 5.10 IUPHAR
Histamine H2 receptor GPCR Kd 6.58 CHEMBL
Histamine H2 receptor Unclassified ANTAGONIST Ki 5.90 IUPHAR

External reference:

IDSource
4018845 VUID
N0000147147 NUI
D00295 KEGG_DRUG
70059-30-2 SECONDARY_CAS_RN
4018844 VANDF
4018845 VANDF
C0008783 UMLSCUI
CHEBI:3699 CHEBI
CHEMBL30 ChEMBL_ID
CHEMBL1201051 ChEMBL_ID
DB00501 DRUGBANK_ID
D002927 MESH_DESCRIPTOR_UI
2756 PUBCHEM_CID
1231 IUPHAR_LIGAND_ID
3765 INN_ID
80061L1WGD UNII
152402 RXNORM
101 MMSL
2261 MMSL
4448 MMSL
4449 MMSL
6098 MMSL
d00140 MMSL
003415 NDDF
004987 NDDF
373541007 SNOMEDCT_US
83051006 SNOMEDCT_US
83532008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 0093-8192 TABLET, FILM COATED 300 mg ORAL ANDA 20 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 0093-8204 TABLET, FILM COATED 400 mg ORAL ANDA 20 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 0093-8305 TABLET, FILM COATED 800 mg ORAL ANDA 20 sections
Good Sense Heartburn Relief HUMAN OTC DRUG LABEL 1 0113-0022 TABLET, FILM COATED 200 mg ORAL ANDA 16 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 0121-0649 SOLUTION 300 mg ORAL ANDA 15 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 0121-1298 SOLUTION 400 mg ORAL ANDA 15 sections
cimetidineacid reducer HUMAN OTC DRUG LABEL 1 0363-0022 TABLET, FILM COATED 200 mg ORAL ANDA 15 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 0378-0053 TABLET, FILM COATED 200 mg ORAL ANDA 20 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 0378-0317 TABLET, FILM COATED 300 mg ORAL ANDA 20 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 0378-0372 TABLET, FILM COATED 400 mg ORAL ANDA 20 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 0378-0541 TABLET, FILM COATED 800 mg ORAL ANDA 20 sections
CIMETIDINE HUMAN PRESCRIPTION DRUG LABEL 1 0440-1282 TABLET 400 mg ORAL ANDA 15 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 10544-626 TABLET, FILM COATED 400 mg ORAL ANDA 20 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 10544-627 TABLET, FILM COATED 300 mg ORAL ANDA 20 sections
CIMETIDINE HUMAN PRESCRIPTION DRUG LABEL 1 16590-048 TABLET, FILM COATED 300 mg ORAL ANDA 17 sections
CIMETIDINE HUMAN PRESCRIPTION DRUG LABEL 1 16590-265 TABLET, FILM COATED 400 mg ORAL ANDA 20 sections
CIMETIDINE HUMAN PRESCRIPTION DRUG LABEL 1 16590-372 TABLET, FILM COATED 800 mg ORAL ANDA 20 sections
CIMETIDINE HUMAN PRESCRIPTION DRUG LABEL 1 21695-531 TABLET 300 mg ORAL ANDA 14 sections
CIMETIDINE HUMAN PRESCRIPTION DRUG LABEL 1 21695-532 TABLET 400 mg ORAL ANDA 14 sections
Good Neighbor Pharmacy Heartburn Relief HUMAN OTC DRUG LABEL 1 24385-111 TABLET, FILM COATED 200 mg ORAL ANDA 16 sections
Acid Reducer HUMAN OTC DRUG LABEL 1 30142-323 TABLET, FILM COATED 200 mg ORAL ANDA 16 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 33261-024 TABLET, FILM COATED 400 mg ORAL ANDA 20 sections
TopCare Heartburn Relief HUMAN OTC DRUG LABEL 1 36800-022 TABLET, FILM COATED 200 mg ORAL ANDA 16 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 42291-217 TABLET, FILM COATED 300 mg ORAL ANDA 20 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 42291-218 TABLET, FILM COATED 400 mg ORAL ANDA 20 sections
Equate Cimetidine HUMAN OTC DRUG LABEL 1 49035-820 TABLET, FILM COATED 200 mg ORAL ANDA 15 sections
SunMark heartburn reliefacid reducer HUMAN OTC DRUG LABEL 1 49348-246 TABLET, FILM COATED 200 mg ORAL ANDA 16 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 50090-0499 TABLET, FILM COATED 300 mg ORAL ANDA 20 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 50090-3574 TABLET, FILM COATED 400 mg ORAL ANDA 21 sections
Cimetidine Hydrochloride Oral Solution HUMAN PRESCRIPTION DRUG LABEL 1 50383-050 SOLUTION 300 mg ORAL ANDA 18 sections