mechlorethamine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
1647 51-75-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • mustine
  • mechlorethamine
  • mustargen
  • nitrogen mustard
  • chlormethine
  • mechlorethamine hydrochloride
  • mechlorethamine HCl
A biologic alkylating agent that exerts its cytotoxic effects by forming DNA ADDUCTS and DNA interstrand crosslinks, thereby inhibiting rapidly proliferating cells. The hydrochloride is an antineoplastic agent used to treat HODGKIN DISEASE and LYMPHOMA.
  • Molecular weight: 156.05
  • Formula: C5H11Cl2N
  • CLOGP: 1.20
  • LIPINSKI: 0
  • HAC: 1
  • HDO: 0
  • TPSA: 3.24
  • ALOGS: -0.67
  • ROTB: 4
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

None

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AKT2,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,ITK,JAK2,JAK3,MAP2K6,MAP3K7,MAPK7,MAPKAPK2,MET,MTOR,NTRK2,PDK2,PDK4,PIM2,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1 38
kinase-selectivity-class AXL,BRAF,CAMK2D,CDK4,EPHB4,GAK,MAPK10,MAPK7,PDK4,PRKCD,SIK2,STK33,TEK 13
pfas-class PFAS structural alert (1 = True, 0 = False) 0

Approvals:

DateAgencyCompanyOrphan
March 15, 1949 FDA RECORDATI RARE

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
Application site pruritus 484.37 51.68 83 1864 4164 90622336
Application site pain 382.41 51.68 69 1878 4651 90621849
Application site erythema 349.91 51.68 65 1882 5143 90621357
Application site discolouration 248.99 51.68 38 1909 900 90625600
Application site irritation 227.83 51.68 39 1908 1922 90624578
Skin discolouration 173.91 51.68 56 1891 44259 90582241
Pruritus 155.92 51.68 112 1835 541413 90085087
Skin irritation 147.64 51.68 38 1909 13565 90612935
Application site vesicles 128.03 51.68 23 1924 1494 90625006
Erythema 121.82 51.68 70 1877 229176 90397324
Application site dryness 109.26 51.68 15 1932 162 90626338
Skin burning sensation 85.93 51.68 27 1920 19584 90606916
Application site discharge 84.93 51.68 12 1935 162 90626338
Therapy non-responder 83.98 51.68 46 1901 136658 90489842
Application site exfoliation 81.09 51.68 13 1934 424 90626076
Application site inflammation 75.44 51.68 12 1935 372 90626128
Cutaneous T-cell lymphoma 70.05 51.68 14 1933 1606 90624894
Skin hyperpigmentation 63.96 51.68 17 1930 6834 90619666
Application site swelling 55.82 51.68 10 1937 637 90625863
Application site rash 52.22 51.68 12 1935 2657 90623843

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
Application site pruritus 503.83 58.09 84 2033 1494 42617724
Application site erythema 450.00 58.09 82 2035 2484 42616734
Application site pain 360.41 58.09 67 2050 2262 42616956
Application site irritation 191.69 58.09 33 2084 707 42618511
Pruritus 190.48 58.09 117 2000 188654 42430564
Skin irritation 180.80 58.09 47 2070 7527 42611691
Application site vesicles 173.84 58.09 30 2087 652 42618566
Therapy non-responder 130.62 58.09 60 2057 53299 42565919
Application site discolouration 120.67 58.09 20 2097 337 42618881
Erythema 118.30 58.09 71 2046 108722 42510496
Application site discharge 113.22 58.09 17 2100 145 42619073
Skin burning sensation 97.90 58.09 29 2088 7458 42611760
Blister 90.08 58.09 38 2079 27452 42591766
Application site erosion 86.45 58.09 13 2104 112 42619106
Application site burn 85.43 58.09 14 2103 219 42618999
Skin discolouration 82.45 58.09 33 2084 20857 42598361
Cutaneous T-cell lymphoma 81.02 58.09 19 2098 1979 42617239
Application site exfoliation 80.15 58.09 13 2104 190 42619028
Second primary malignancy 78.66 58.09 26 2091 9549 42609669
Application site swelling 73.30 58.09 13 2104 331 42618887
Application site reaction 70.84 58.09 13 2104 403 42618815
Disease progression 65.01 58.09 55 2062 143601 42475617
Application site scab 61.25 58.09 9 2108 65 42619153
Dermatitis 58.32 58.09 22 2095 11853 42607365
Application site dryness 58.28 58.09 9 2108 94 42619124

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
Application site pruritus 979.81 48.39 163 3830 3997 110581309
Application site erythema 804.41 48.39 144 3849 5466 110579840
Application site pain 715.28 48.39 130 3863 5369 110579937
Application site irritation 421.22 48.39 71 3922 1866 110583440
Application site discolouration 338.58 48.39 54 3939 995 110584311
Pruritus 322.89 48.39 220 3773 581340 110003966
Skin irritation 309.34 48.39 79 3914 16240 110569066
Application site vesicles 282.89 48.39 49 3944 1515 110583791
Skin discolouration 231.22 48.39 81 3912 48965 110536341
Erythema 224.56 48.39 136 3857 291311 110293995
Therapy non-responder 205.28 48.39 104 3889 157203 110428103
Application site discharge 192.25 48.39 29 3964 363 110584943
Skin burning sensation 179.66 48.39 55 3938 21770 110563536
Application site dryness 162.62 48.39 24 3969 256 110585050
Application site exfoliation 138.52 48.39 23 3970 547 110584759
Cutaneous T-cell lymphoma 135.34 48.39 30 3963 3354 110581952
Application site swelling 128.36 48.39 23 3970 864 110584442
Disease progression 114.93 48.39 84 3909 243950 110341356
Application site erosion 112.86 48.39 18 3975 330 110584976
Application site reaction 109.74 48.39 20 3973 827 110584479
Application site inflammation 107.77 48.39 18 3975 444 110584862
Skin hyperpigmentation 102.66 48.39 29 3964 8667 110576639
Application site burn 99.81 48.39 19 3974 998 110584308
Dermatitis 97.58 48.39 37 3956 27800 110557506
Application site rash 94.01 48.39 21 3972 2429 110582877
Application site scab 90.05 48.39 14 3979 216 110585090
Dry skin 84.45 48.39 51 3942 107602 110477704
Blister 73.97 48.39 63 3930 227313 110357993
Cutaneous T-cell lymphoma recurrent 68.89 48.39 10 3983 94 110585212
Skin exfoliation 67.37 48.39 41 3952 87610 110497696
Second primary malignancy 63.25 48.39 24 3969 18044 110567262
Scab 58.97 48.39 21 3972 13215 110572091
Application site haemorrhage 58.36 48.39 13 3980 1483 110583823
Lymphomatoid papulosis 55.06 48.39 10 3983 405 110584901
Dermatitis contact 50.52 48.39 19 3974 13934 110571372
Skin lesion 49.81 48.39 28 3965 51603 110533703
Skin disorder 48.95 48.39 26 3967 42887 110542419

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC L01AA05 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ALKYLATING AGENTS
Nitrogen mustard analogues
FDA MoA N0000000236 Alkylating Activity
FDA EPC N0000175558 Alkylating Drug
MeSH PA D000477 Alkylating Agents
MeSH PA D000970 Antineoplastic Agents
MeSH PA D002619 Chemical Warfare Agents
MeSH PA D007509 Irritants
MeSH PA D011042 Poisons
MeSH PA D018906 Antineoplastic Agents, Alkylating
CHEBI has role CHEBI:22333 alkylating agent
CHEBI has role CHEBI:35610 antineoplastic agent

Related Drugs by ATC class:

L01AA Nitrogen mustard analogues 8 drugs
bendamustinechlorambucilcyclophosphamideifosfamidemelphalanmelphalan flufenamideprednimustinetrofosfamide

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Chronic lymphoid leukemia, disease indication 92814006
Chronic myeloid leukemia indication 92818009 DOID:8552
Polycythemia vera indication 109992005
Hodgkin's disease indication 118599009
Non-Hodgkin's lymphoma indication 118601006
Mycosis fungoides indication 118618005
Malignant tumor of lung indication 363358000
Primary cutaneous T-cell lymphoma indication 400122007
Pericardial Malignant Effusions indication
Peritoneal Malignant Effusions indication
Pleural Malignant Effusions indication
Amyloidosis contraindication 17602002 DOID:9120
Hyperuricemia contraindication 35885006 DOID:1920
Acute infectious disease contraindication 63171007
Blood coagulation disorder contraindication 64779008 DOID:1247
Leukopenia contraindication 84828003 DOID:615
Secondary malignant neoplasm of bone marrow contraindication 94217008
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Bone marrow depression contraindication 307762000
Breastfeeding (mother) contraindication 413712001
Granulocytopenic disorder contraindication 417672002
Chemotherapy-Induced Hyperuricemia contraindication




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 5.7 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 0.016% BASE VALCHLOR HELSINN N202317 Aug. 23, 2013 RX GEL TOPICAL 8501819 March 7, 2026 ALKYLATING DRUG INDICATED FOR THE TOPICAL TREATMENT OF STAGE IA AND IB MYCOSIS FUNGOIDES-TYPE CUTANEOUS T-CELL LYMPHOMA IN PATIENTS WHO HAVE RECEIVED PRIOR SKIN DIRECTED THERAPY
EQ 0.016% BASE VALCHLOR HELSINN N202317 Aug. 23, 2013 RX GEL TOPICAL 7872050 July 8, 2029 ALKYLATING DRUG INDICATED FOR THE TOPICAL TREATMENT OF STAGE IA AND IB MYCOSIS FUNGOIDES-TYPE CUTANEOUS T-CELL LYMPHOMA IN PATIENTS WHO HAVE RECEIVED PRIOR SKIN DIRECTED THERAPY

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

None

External reference:

IDSource
4019808 VUID
N0000147897 NUI
D04872 KEGG_DRUG
55-86-7 SECONDARY_CAS_RN
4017994 VANDF
4019808 VANDF
C0025033 UMLSCUI
CHEBI:28925 CHEBI
CHEMBL427 ChEMBL_ID
DB00888 DRUGBANK_ID
CHEMBL1201001 ChEMBL_ID
D008466 MESH_DESCRIPTOR_UI
4033 PUBCHEM_CID
586 INN_ID
7218 IUPHAR_LIGAND_ID
50D9XSG0VR UNII
155036 RXNORM
1972 MMSL
29634 MMSL
5028 MMSL
d01339 MMSL
002630 NDDF
004816 NDDF
29156002 SNOMEDCT_US
372692002 SNOMEDCT_US
387071000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
VALCHLOR HUMAN PRESCRIPTION DRUG LABEL 1 69639-120 GEL 0.01 g TOPICAL NDA 28 sections