Cilastatin
Highest phase reached
Approved
Drug type
Small molecule
First approval year
1985
- First approval year
- 1985
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Cilastatin
- Molecular weight
- 358.46
- Structure (SMILES)
- CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N)C(=O)O)C(=O)O
- cilastatin
- Cilastatin
- cilastatin [INN]
- CILASTATIN [MI]
- CILASTATIN [VANDF]
- Cilastatin [WHO-DD]
- cilastatin inn
- cilastatin mi
- cilastatin vandf
- cilastatin who dd
- cilastatina
- Cilastatina
- cilastatine
- Cilastatine
- primaxin
- Primaxin
- primaxin iv 500 mg powder for solution for infusion
- CAS registry numbers
- 82009-34-5
- ChEMBL ID
- CHEMBL766
- InChIKey
- DHSUYTOATWAVLW-WFVMDLQDSA-N
- PubChem compound IDs
- 6435415
- RxNorm IDs (RxCUI)
- 2540
- FDA ingredient codes (UNII)
- 141A6AMN38
- Applicant
- MERCK
- Approval date
- 26 Nov 1985
- Application number
- NDA050587
- First in class
- No
- Orphan designation
- No
- Availability
- Prescription only
- United States (FDA)
- Approved
- Pharmacology name
- cilastatin
- Type
- Synthetic organic
- Drug name stem
- -stat-
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Parenteral
Mechanisms of action
- Mechanism
- Renal dipeptidase inhibitor
- Action type
- Inhibitor
- Target
- Dipeptidase 1
- Protein identifier
- P16444
Open Targets mechanisms
- Mechanism
- Renal dipeptidase inhibitor
- Action type
- Inhibitor
- Target
- Dipeptidase 1
DrugCentral mechanisms
- Action type
- Inhibitor
- Gene symbol
- DPEP1
- Protein identifier
- P16444
- Organism
- Homo sapiens
- Target development level
- Clinical
- Condition
- Infections
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000544
- Subject identifier
- D007239
- Condition
- Bacterial Infections
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000771
- Subject identifier
- D001424
- Condition
- Osteomyelitis
- Highest recorded phase
- 0.5
- Condition identifier
- EFO:0003102
- Subject identifier
- D010019
- Condition
- Urinary Tract Infections
- Highest recorded phase
- 3
- Condition identifier
- EFO:0003103
- Subject identifier
- D014552
- Condition
- Pyelonephritis
- Highest recorded phase
- 3
- Condition identifier
- EFO:1001141
- Subject identifier
- D011704
- Condition
- Pneumonia, Bacterial
- Highest recorded phase
- 3
- Condition identifier
- EFO:1001272
- Subject identifier
- D018410
- Condition
- Pneumonia, Ventilator-Associated
- Highest recorded phase
- 3
- Condition identifier
- EFO:1001865
- Subject identifier
- D053717
- Condition
- Sepsis
- Highest recorded phase
- 1
- Condition identifier
- HP:0100806
- Subject identifier
- D018805
- Condition
- Hematologic Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- MONDO:0044881
- Subject identifier
- D019337
- Condition identifier
- EFO_0000544
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000771
- Condition identifier
- EFO_0003102
- Condition identifier
- EFO_0003103
- Highest recorded phase
- 3
- Condition identifier
- EFO_0011056
- Highest recorded phase
- 2
- Condition identifier
- EFO_1001272
- Highest recorded phase
- 3
- Condition identifier
- EFO_1001865
- Highest recorded phase
- 3
- Condition identifier
- HP_0100523
- Highest recorded phase
- 3
- Condition identifier
- HP_0100806
- Highest recorded phase
- 1
- Condition identifier
- MONDO_0003529
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0005113
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0005249
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0021678
- Condition identifier
- MONDO_0021678
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0100338
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0700051
- Highest recorded phase
- 3
- Event
- agranulocytosis
- Reports
- 17
- Reporting signal score
- 26.49
- Event
- anaphylactic shock
- Reports
- 10
- Reporting signal score
- 10.5639
- Event
- arthralgia
- Reports
- 1
- Reporting signal score
- 12.4553
- Event
- asthenia
- Reports
- 2
- Reporting signal score
- 9.65954
- Event
- blood alkaline phosphatase increased
- Reports
- 13
- Reporting signal score
- 14.2596
- Event
- burkholderia cepacia infection
- Reports
- 2
- Reporting signal score
- 11.3259
- Event
- candidiasis
- Reports
- 5
- Reporting signal score
- 10.669
- Event
- cholestasis
- Reports
- 12
- Reporting signal score
- 14.5133
- Event
- clostridial infection
- Reports
- 5
- Reporting signal score
- 10.7978
- Event
- clostridium colitis
- Reports
- 5
- Reporting signal score
- 15.5378
- Event
- clostridium difficile colitis
- Reports
- 8
- Reporting signal score
- 12.7283
- Event
- convulsion
- Reports
- 123
- Reporting signal score
- 310.695
- Event
- cutaneous vasculitis
- Reports
- 4
- Reporting signal score
- 8.99697
- Event
- cytolytic hepatitis
- Reports
- 11
- Reporting signal score
- 27.0922
- Event
- depressed level of consciousness
- Reports
- 12
- Reporting signal score
- 9.322
- Event
- dermatitis exfoliative
- Reports
- 13
- Reporting signal score
- 30.5494
- Event
- dizziness
- Reports
- 3
- Reporting signal score
- 12.3328
- Event
- drug rash with eosinophilia and systemic symptoms
- Reports
- 15
- Reporting signal score
- 41.4902
- Event
- eosinophilia
- Reports
- 21
- Reporting signal score
- 39.1356
- Event
- epilepsy
- Reports
- 17
- Reporting signal score
- 22.4673
- Event
- extradural abscess
- Reports
- 3
- Reporting signal score
- 8.99459
- Event
- gamma-glutamyltransferase increased
- Reports
- 17
- Reporting signal score
- 23.0236
- Event
- grand mal convulsion
- Reports
- 19
- Reporting signal score
- 42.7516
- Event
- headache
- Reports
- 3
- Reporting signal score
- 15.8482
- Event
- intrauterine infection
- Reports
- 3
- Reporting signal score
- 14.4538
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- Dose
- 1.25 grams (imipenem 500 mg, cilastatin 500 mg, relebactam 250 mg)
- Route
- Intravenous
- How often
- Every 6 hours
- Hydrogen bond acceptors
- 5
- Hydrogen bond donors
- 4
- Polar surface area
- 129.72
- Calculated partition coefficient (ALogP)
- 1.43
- Calculated partition coefficient (XLogP)
- -1
- Prodrug
- No
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 11
- Heavy atoms
- 24
- Molecular formula
- C16H26N2O5S
- Monoisotopic mass
- 358.15624311
- Natural product
- Yes
- 0006-3856
- Recorded assays
- 191
- Active assays
- 4
Active assay types
- Confirmatory
- Protease Inhibitors
Related records
Trials (35)
- A Double-blind Non Inferiority Clinical Trial to Compare the Nephroprotection of Cilastatn Versus Thiosulfate in Patients Undergoing Debulking Surgery With Intraoperative Hyperthermic Intraperitoneal Chemotherapy With Cisplatin.
- A Safety and Tolerability Study of Doripenem in Patients With Abdominal Infections or Pneumonia
- A Single-Dose Study to Investigate the Pharmacokinetics of MK-7655 in Participants With Impaired Renal Function (MK-7655-005)
- A Study of Efficacy and Safety of Intravenous Cefiderocol (S-649266) Versus Imipenem/Cilastatin in Complicated Urinary Tract Infections
- A Study of Oral Tebipenem Pivoxil Hydrobromide (TBP-PI-HBr) Compared to Intravenous Imipenem-cilastatin in Participants With Complicated Urinary Tract Infection (cUTI) or Acute Pyelonephritis (AP)
- A Study of the Safety and Effectiveness of Levofloxacin Compared With Imipenem/Cilastatin in Patients With Pneumonia Acquired During Hospitalization
- A Study To Determine The Efficacy And Safety Of Tigecycline Compared With Imipenem/Cliastatin to Treat Complicated Intra-Abdominal Infection
- Bacteriophage Therapy for Mycobacterium Abscessus Pulmonary Infection
- Comparative Study of NXL104/Ceftazidime Versus Comparator in Adults With Complicated Urinary Tract Infections
- Comparing Efficacy and Safety of (Meropenem + Colistin) Versus (Imipenem/Cilastatin + Tigecycline) on Eradication of Multi-Drug Resistance Bacteria
- Complicated Skin and Skin Structure Infections
- Efficacy and Safety of Cefepime/Nacubactam or Aztreonam/Nacubactam Compared to Imipenem/Cilastatin in Subjects With Complicated Urinary Tract Infections or Acute Uncomplicated Pyelonephritis
- Efficacy and Safety of Imipenem+Cilastatin/Relebactam (MK-7655A) in Japanese Participants With Complicated Intra-abdominal Infection or Complicated Urinary Tract Infection (MK-7655A-017)
- Efficacy and Safety of Imipenem+Cilastatin/Relebactam (MK-7655A) Versus Colistimethate Sodium+Imipenem+Cilastatin in Imipenem-Resistant Bacterial Infection (MK-7655A-013)
- Evaluation of Safety and Efficacy of Intravenous Sulbactam-ETX2514 in the Treatment of Hospitalized Adults With Complicated Urinary Tract Infections
- Evaluation of the Safety, Tolerability and Pharmacokinetics of Intravenous ETX2514 Administered in Healthy Subjects
- GSK2251052 in Complicated Urinary Tract Infection
- Imipenem/Cilastatin-XNW4107 Versus Imipenem/Cilastatin/Relebactam for Treatment of Participants With Bacterial Pneumonia (XNW4107-302, REITAB-2)
- Imipenem/Cilastatin/Relebactam Pharmacokinetics, Safety, and Outcomes in Adults and Adolescents With Cystic Fibrosis
- Imipenem/Cilastatin/Relebactam PK in ECMO
Approved for (1)
In development for (9)
- Acute pyelonephritis Phase 3
- Bacterial infectious disease Phase 3
- Bacterial pneumonia Phase 3
- Hematopoietic and lymphoid cell neoplasm Phase 2
- Liver abscess (disease) Phase 3
- Osteomyelitis Early phase 1
- Pneumonia Phase 3
- Pyelonephritis Phase 3
- Urinary tract infection Phase 3
Targets (1)
- DPEP1 Renal dipeptidase inhibitor