cimetidine ๐Ÿถ Veterinary Use | 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 ยตM/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 141.13 13.18 56 13833 6182 50585053
Urine leukocyte esterase positive 121.71 13.18 41 13848 2842 50588393
Body tinea 111.63 13.18 32 13857 1295 50589940
Inhibitory drug interaction 95.22 13.18 32 13857 2201 50589034
Infection susceptibility increased 90.64 13.18 32 13857 2552 50588683
Lymphocyte count decreased 80.81 13.18 63 13826 26244 50564991
Glucose tolerance impaired 72.61 13.18 33 13856 5085 50586150
Impaired quality of life 67.32 13.18 33 13856 6023 50585212
Culture urine positive 64.43 13.18 27 13862 3424 50587811
Urine ketone body present 63.63 13.18 24 13865 2309 50588926
Purpura 57.17 13.18 35 13854 9876 50581359
Chronic kidney disease 56.70 13.18 62 13827 39709 50551526
Hyperlipidaemia 56.13 13.18 43 13846 17447 50573788
Blood urine present 55.95 13.18 38 13851 12795 50578440
Poor quality sleep 51.40 13.18 40 13849 16606 50574629
Bone density decreased 51.17 13.18 34 13855 11041 50580194
Anaphylactoid reaction 48.44 13.18 22 13867 3384 50587851
Drug intolerance 48.26 13.18 3 13886 219101 50372134
Erythema 43.17 13.18 112 13777 146302 50444933
Impaired work ability 40.43 13.18 32 13857 13608 50577627
Neutrophil count increased 37.22 13.18 31 13858 14164 50577071
Joint swelling 36.51 13.18 11 13878 245275 50345960
Torsade de pointes 35.59 13.18 28 13861 11807 50579428
Oral herpes 34.31 13.18 35 13854 20690 50570545
Rheumatoid arthritis 34.17 13.18 7 13882 202543 50388692
Skin disorder 31.73 13.18 36 13853 23994 50567241
Hypertension 31.54 13.18 128 13761 211075 50380160
Drug ineffective 31.20 13.18 118 13771 819215 49772020
Bacterial test positive 30.66 13.18 18 13871 4705 50586530
Band sensation 29.86 13.18 10 13879 680 50590555
Keratitis 28.99 13.18 14 13875 2471 50588764
Tri-iodothyronine free decreased 28.44 13.18 8 13881 302 50590933
Creatinine urine decreased 27.92 13.18 7 13882 168 50591067
Infusion site scar 27.80 13.18 8 13881 328 50590907
Red cell distribution width increased 27.36 13.18 21 13868 8538 50582697
Specific gravity urine decreased 25.98 13.18 9 13880 678 50590557
Urticaria 25.60 13.18 86 13803 129475 50461760
Cataract 23.96 13.18 45 13844 47255 50543980
Infusion site discomfort 23.83 13.18 9 13880 869 50590366
Anxiety 23.67 13.18 104 13785 177502 50413733
Product use issue 23.53 13.18 6 13883 149469 50441766
Electrocardiogram T wave amplitude decreased 23.20 13.18 7 13882 339 50590896
Insomnia 23.00 13.18 102 13787 174763 50416472
Product dose omission issue 22.76 13.18 11 13878 183827 50407408
Cellulitis 22.75 13.18 56 13833 70742 50520493
Circulatory collapse 21.52 13.18 27 13862 19973 50571262
Red blood cell count decreased 20.75 13.18 35 13854 33800 50557435
Basophil count increased 20.68 13.18 8 13881 824 50590411
Alanine aminotransferase increased 20.50 13.18 62 13827 88297 50502938
Therapeutic product effect decreased 20.41 13.18 6 13883 136044 50455191
Death 19.93 13.18 155 13734 325224 50266011
Blood thyroid stimulating hormone increased 19.59 13.18 15 13874 6077 50585158
Peripheral swelling 19.15 13.18 17 13872 205919 50385316
Red blood cells urine positive 19.14 13.18 11 13878 2764 50588471
Protein urine present 18.98 13.18 14 13875 5363 50585872
Food interaction 18.81 13.18 7 13882 649 50590586
Arthropathy 18.71 13.18 10 13879 157896 50433339
Palmar-plantar erythrodysaesthesia syndrome 18.31 13.18 25 13864 20073 50571162
Contraindicated product administered 18.30 13.18 9 13880 148949 50442286
Chromaturia 17.82 13.18 21 13868 14569 50576666
White blood cell count decreased 17.60 13.18 71 13818 116651 50474584
C-reactive protein abnormal 17.36 13.18 29 13860 27780 50563455
Wound 17.13 13.18 4 13885 105790 50485445
Infusion site rash 17.00 13.18 8 13881 1334 50589901
Urobilinogen urine increased 16.76 13.18 5 13884 233 50591002
Systemic lupus erythematosus 16.52 13.18 9 13880 140613 50450622
Infusion site warmth 16.49 13.18 8 13881 1426 50589809
Flushing 16.47 13.18 48 13841 66967 50524268
Nitrite urine present 16.46 13.18 7 13882 920 50590315
Pancreatitis acute 16.45 13.18 26 13863 23786 50567449
Maternal exposure during pregnancy 16.34 13.18 12 13877 159766 50431469
Thyroid cyst 16.01 13.18 6 13883 567 50590668
Feeling hot 15.90 13.18 34 13855 39168 50552067
Red cell distribution width decreased 15.28 13.18 7 13882 1098 50590137
Glucose urine present 14.93 13.18 6 13883 684 50590551
Drug exposure before pregnancy 14.61 13.18 6 13883 723 50590512
Immune thrombocytopenia 14.51 13.18 15 13874 9002 50582233
Monocyte count decreased 14.42 13.18 8 13881 1878 50589357
pH urine increased 14.35 13.18 5 13884 383 50590852
Abdominal discomfort 13.50 13.18 27 13862 231614 50359621
Ventricular tachycardia 13.40 13.18 19 13870 15802 50575433

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 33.78 16.02 38 5572 36378 29532539
Renal injury 19.75 16.02 16 5594 10186 29558731
Palmar-plantar erythrodysaesthesia syndrome 18.32 16.02 18 5592 14741 29554176
Peptic ulcer 18.02 16.02 9 5601 2476 29566441

FDA Adverse Event Reporting System (Geriatric)

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 150.32 13.17 60 16255 7302 64475115
Urine leukocyte esterase positive 118.31 13.17 41 16274 3362 64479055
Body tinea 110.46 13.17 31 16284 1262 64481155
Lymphocyte count decreased 88.37 13.17 77 16238 40622 64441795
Infection susceptibility increased 87.70 13.17 31 16284 2695 64479722
Inhibitory drug interaction 86.18 13.17 33 16282 3594 64478823
Urine ketone body present 71.16 13.17 28 16287 3279 64479138
Glucose tolerance impaired 64.93 13.17 32 16283 6411 64476006
Impaired quality of life 64.80 13.17 32 16283 6439 64475978
Culture urine positive 61.74 13.17 27 16288 4124 64478293
Bone density decreased 54.47 13.17 33 16282 9919 64472498
Poor quality sleep 51.83 13.17 41 16274 18910 64463507
Hyperlipidaemia 50.93 13.17 44 16271 22932 64459485
Blood urine present 46.59 13.17 38 16277 18302 64464115
Purpura 46.50 13.17 37 16278 17209 64465208
Erythema 44.91 13.17 126 16189 186944 64295473
Anaphylactoid reaction 43.23 13.17 22 16293 4716 64477701
Hypertension 41.58 13.17 152 16163 259109 64223308
Torsade de pointes 35.97 13.17 32 16283 17331 64465086
Impaired work ability 35.47 13.17 30 16285 15189 64467228
Red cell distribution width increased 34.45 13.17 27 16288 12282 64470135
Oral herpes 32.93 13.17 34 16281 22118 64460299
Urticaria 31.27 13.17 95 16220 147222 64335195
Palmar-plantar erythrodysaesthesia syndrome 30.42 13.17 37 16278 28782 64453635
Infusion site scar 30.33 13.17 8 16307 257 64482160
Keratitis 29.44 13.17 15 16300 3222 64479195
Skin disorder 28.35 13.17 35 16280 27645 64454772
Tri-iodothyronine free decreased 27.88 13.17 8 16307 353 64482064
Chronic kidney disease 27.31 13.17 51 16264 57868 64424549
Flushing 27.29 13.17 61 16254 78587 64403830
Red blood cell count decreased 27.18 13.17 46 16269 48340 64434077
Band sensation 26.94 13.17 9 16306 660 64481757
Bacterial test positive 26.26 13.17 18 16297 6672 64475745
Alanine aminotransferase increased 26.15 13.17 86 16229 138945 64343472
Joint swelling 25.94 13.17 11 16304 215371 64267046
Infusion site discomfort 25.74 13.17 9 16306 757 64481660
Specific gravity urine decreased 25.55 13.17 9 16306 774 64481643
Off label use 25.49 13.17 79 16236 632727 63849690
Insomnia 25.23 13.17 108 16207 197728 64284689
Cataract 22.76 13.17 44 16271 51218 64431199
Monocyte count decreased 22.44 13.17 12 16303 2845 64479572
Peptic ulcer 22.41 13.17 15 16300 5348 64477069
Creatinine urine decreased 21.98 13.17 6 16309 220 64482197
Secondary adrenocortical insufficiency 21.72 13.17 11 16304 2334 64480083
Drug ineffective 21.43 13.17 125 16190 840122 63642295
Ventricular tachycardia 21.16 13.17 34 16281 34231 64448186
Basophil count increased 21.12 13.17 9 16306 1291 64481126
Contusion 20.98 13.17 70 16245 113895 64368522
Neutrophil count increased 19.85 13.17 28 16287 25146 64457271
Infusion site warmth 19.35 13.17 8 16307 1064 64481353
White blood cell count decreased 19.22 13.17 85 16230 157752 64324665
Red cell distribution width decreased 19.20 13.17 8 16307 1085 64481332
Dyspepsia 19.14 13.17 54 16261 80258 64402159
Infusion site rash 19.11 13.17 8 16307 1098 64481319
Rheumatoid arthritis 18.82 13.17 9 16306 164285 64318132
Mean cell haemoglobin increased 18.51 13.17 11 16304 3191 64479226
Haematocrit increased 18.06 13.17 11 16304 3334 64479083
Blood thyroid stimulating hormone increased 17.65 13.17 15 16300 7639 64474778
Protein urine present 17.55 13.17 16 16299 8940 64473477
Anxiety 17.49 13.17 99 16216 202550 64279867
Drug exposure before pregnancy 17.34 13.17 6 16309 489 64481928
Therapeutic product effect decreased 17.25 13.17 4 16311 115347 64367070
Gastrooesophageal reflux disease 17.05 13.17 53 16262 83090 64399327
Therapeutic product effect incomplete 16.69 13.17 3 16312 103479 64378938
Leukocyturia 16.58 13.17 8 16307 1530 64480887
Electrocardiogram T wave amplitude decreased 16.57 13.17 6 16309 559 64481858
Nitrite urine present 16.03 13.17 7 16308 1065 64481352
Peripheral swelling 15.54 13.17 18 16297 209135 64273282
C-reactive protein abnormal 15.50 13.17 27 16288 29020 64453397
Product dose omission issue 15.30 13.17 16 16299 194731 64287686
Infusion site pruritus 15.19 13.17 9 16306 2597 64479820
Eosinophil count increased 14.70 13.17 18 16297 14094 64468323
Thyroid cyst 14.69 13.17 5 16310 388 64482029
Blood alkaline phosphatase increased 14.56 13.17 39 16276 56240 64426177
pH urine increased 14.20 13.17 5 16310 429 64481988
Aspartate aminotransferase increased 14.19 13.17 64 16251 119724 64362693
Food interaction 13.94 13.17 7 16308 1459 64480958
Duodenal ulcer haemorrhage 13.78 13.17 12 16303 6313 64476104
Cellulitis 13.39 13.17 53 16262 93604 64388813
Product use in unapproved indication 13.33 13.17 15 16300 176603 64305814
White blood cells urine positive 13.32 13.17 11 16304 5387 64477030

FDA Adverse Event Reporting System (Pediatric)

None

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
CHEBI has role CHEBI:37961 H2 receptor antagonists
CHEBI has role CHEBI:49201 anti-ulcer drugs
CHEBI has role CHEBI:50183 P450 inhibitors
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
FDA EPC N0000175784 Histamine-2 Receptor Antagonist

Drug Use | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
5-hydroxytryptamine receptor 2A GPCR Ki 5.16 PDSP
Multidrug and toxin extrusion protein 1 Transporter IC50 5.92 CHEMBL
Multidrug and toxin extrusion protein 2 Transporter INHIBITOR Ki 5.10 IUPHAR
Histamine H2 receptor GPCR Kd 6.58 CHEMBL
Histamine H2 receptor GPCR ANTAGONIST Ki 5.90 IUPHAR

External reference:

IDSource
4018845 VUID
N0000147147 NUI
D00295 KEGG_DRUG
70059-30-2 SECONDARY_CAS_RN
152402 RXNORM
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
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 0093-8192 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 0093-8204 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
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 0121-0649 SOLUTION 300 mg ORAL ANDA 15 sections
Cimetidine HUMAN PRESCRIPTION DRUG LABEL 1 0121-1298 SOLUTION 400 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
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