GEMCITABINE HYDROCHLORIDE

Search structure
Trade Names:
Synonyms:
Status: Approved (1996)
Entry Type: Small molecule
Molecule Category: Salt Prodrug
UNII: U347PV74IL
Parent Compound: GEMCITABINE

Structure
InChI Key OKKDEIYWILRZIA-OSZBKLCCSA-N
Smile Cl.Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)C2(F)F)c(=O)n1
InChI
InChI=1S/C9H11F2N3O4.ClH/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17;/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17);1H/t4-,6-,7-;/m1./s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C9H12ClF2N3O4
Molecular Weight 299.66
AlogP -1.29
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 2.0
Polar Surface Area 110.6
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 18.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA polymerase (alpha/delta/epsilon) inhibitor DailyMed

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Carcinoma, Non-Small-Cell Lung 4 D002289 ClinicalTrials
Neoplasms 3 D009369 ClinicalTrials
Urinary Bladder Neoplasms 3 D001749 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Triple Negative Breast Neoplasms 3 D064726 ClinicalTrials
Uterine Cervical Neoplasms 3 D002583 ClinicalTrials
Urinary Bladder Neoplasms 3 D001749 ClinicalTrials
Thromboembolism 3 D013923 ClinicalTrials
Urinary Bladder Neoplasms 3 D001749 ClinicalTrials
Uterine Cervical Neoplasms 3 D002583 ClinicalTrials
Urethral Neoplasms 3 D014523 ClinicalTrials
Gallbladder Neoplasms 3 D005706 ClinicalTrials
Lung Neoplasms 3 D008175 ClinicalTrials
Neoplasms 3 D009369 ClinicalTrials
Carcinoma, Squamous Cell 3 D002294 ClinicalTrials
Breast Neoplasms, Male 2 D018567 ClinicalTrials
Lymphoma, Mantle-Cell 2 D020522 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Liver Neoplasms 2 D008113 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Hodgkin Disease 2 D006689 ClinicalTrials
Carcinoma 2 D002277 ClinicalTrials
Carcinoma, Endometrioid 2 D018269 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Carcinoma, Pancreatic Ductal 2 D021441 ClinicalTrials
Nasopharyngeal Neoplasms 2 D009303 ClinicalTrials
Head and Neck Neoplasms 2 D006258 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Leukemia, Plasma Cell 2 D007952 ClinicalTrials
Plasmacytoma 2 D010954 ClinicalTrials
Mesothelioma 2 D008654 ClinicalTrials
Leukemia 2 D007938 ClinicalTrials
Cystadenoma, Serous 2 D018293 ClinicalTrials
Retroviridae Infections 2 D012192 ClinicalTrials
Cholangiocarcinoma 2 D018281 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Ureteral Neoplasms 2 D014516 ClinicalTrials
Peritoneal Neoplasms 2 D010534 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Kidney Neoplasms 2 D007680 ClinicalTrials
Hereditary Breast and Ovarian Cancer Syndrome 1 D061325 ClinicalTrials
Lymphoma, Follicular 1 D008224 ClinicalTrials
Uterine Neoplasms 1 D014594 ClinicalTrials
Klatskin Tumor 1 D018285 ClinicalTrials
Lymphoma, T-Cell 1 D016399 ClinicalTrials
Mycosis Fungoides 1 D009182 ClinicalTrials
Endometrial Neoplasms 1 D016889 ClinicalTrials
Stomach Neoplasms 1 D013274 ClinicalTrials
Carcinoma, Renal Cell 1 D002292 ClinicalTrials
Lymphoproliferative Disorders 1 D008232 ClinicalTrials

Related Entries

Scaffolds

Parent

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
12.87
Blood and lymphatic system disorders
12.82
Gastrointestinal disorders
9.13
Vascular disorders
7.69
Respiratory, thoracic and mediastinal disorders
7.3
Nervous system disorders
5.42
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
5.08
Injury, poisoning and procedural complications
5.0
Cardiac disorders
4.86
Investigations
4.47
Skin and subcutaneous tissue disorders
4.27
Infections and infestations
4.26
Renal and urinary disorders
3.77
Metabolism and nutrition disorders
3.36
Hepatobiliary disorders
2.73
Musculoskeletal and connective tissue disorders
2.12

Cross References

Resources Reference
ChEBI 31647
ChEMBL CHEMBL1637
EPA CompTox DTXSID3047849
FDA SRS U347PV74IL
PubChem 60749
SureChEMBL SCHEMBL4366
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