mechlorethamine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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

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 433.24 53.39 80 1725 3679 50599640
Application site pain 356.29 53.39 68 1737 3730 50599589
Application site erythema 320.02 53.39 64 1741 4474 50598845
Application site discolouration 231.00 53.39 37 1768 713 50602606
Application site irritation 196.17 53.39 36 1769 1579 50601740
Skin discolouration 158.82 53.39 55 1750 32702 50570617
Pruritus 155.77 53.39 106 1699 283462 50319857
Skin irritation 144.94 53.39 37 1768 7690 50595629
Erythema 112.86 53.39 68 1737 146346 50456973
Application site vesicles 112.84 53.39 22 1783 1333 50601986
Therapy non-responder 104.94 53.39 46 1759 50976 50552343
Application site dryness 102.27 53.39 15 1790 155 50603164
Skin burning sensation 81.32 53.39 25 1780 10160 50593159
Application site discharge 79.56 53.39 12 1793 152 50603167
Application site exfoliation 72.36 53.39 12 1793 287 50603032
Application site inflammation 62.71 53.39 11 1794 370 50602949
Skin hyperpigmentation 59.83 53.39 17 1788 5259 50598060

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 477.16 65.54 81 1840 1216 29571390
Application site erythema 418.98 65.54 78 1843 2021 29570585
Application site pain 364.47 65.54 67 1854 1612 29570994
Pruritus 211.03 65.54 116 1805 116733 29455873
Application site irritation 187.97 65.54 33 1888 601 29572005
Skin irritation 182.86 65.54 45 1876 4416 29568190
Application site vesicles 172.70 65.54 30 1891 512 29572094
Therapy non-responder 146.73 65.54 60 1861 30851 29541755
Application site discolouration 124.64 65.54 20 1901 204 29572402
Erythema 122.02 65.54 70 1851 75536 29497070
Skin burning sensation 110.67 65.54 29 1892 3644 29568962
Application site discharge 94.67 65.54 15 1906 140 29572466
Blister 88.72 65.54 37 1884 19869 29552737
Skin discolouration 83.63 65.54 33 1888 15376 29557230
Application site burn 83.01 65.54 14 1907 198 29572408
Cutaneous T-cell lymphoma 78.78 65.54 18 1903 1275 29571331
Application site exfoliation 77.27 65.54 12 1909 97 29572509
Application site swelling 74.66 65.54 13 1908 224 29572382
Application site erosion 73.14 65.54 11 1910 70 29572536
Disease progression 70.14 65.54 51 1870 81865 29490741

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 897.17 47.30 158 3548 3381 64491645
Application site erythema 732.09 47.30 139 3567 4550 64490476
Application site pain 682.35 47.30 129 3577 4119 64490907
Application site irritation 389.61 47.30 69 3637 1507 64493519
Pruritus 337.10 47.30 213 3493 312187 64182839
Application site discolouration 333.84 47.30 54 3652 666 64494360
Skin irritation 302.94 47.30 76 3630 9118 64485908
Application site vesicles 268.40 47.30 49 3657 1273 64493753
Therapy non-responder 245.70 47.30 104 3602 65795 64429231
Skin discolouration 216.94 47.30 80 3626 35175 64459851
Erythema 214.36 47.30 133 3573 186937 64308089
Skin burning sensation 184.77 47.30 53 3653 10530 64484496
Application site discharge 171.21 47.30 27 3679 279 64494747
Application site dryness 161.55 47.30 24 3682 160 64494866
Application site exfoliation 126.22 47.30 21 3685 310 64494716
Application site swelling 118.70 47.30 22 3684 620 64494406
Cutaneous T-cell lymphoma 116.26 47.30 27 3679 2325 64492701
Disease progression 107.07 47.30 78 3628 141602 64353424
Blister 101.07 47.30 61 3645 80906 64414120
Application site erosion 97.98 47.30 16 3690 209 64494817
Skin hyperpigmentation 97.47 47.30 29 3677 6522 64488504
Application site burn 95.65 47.30 19 3687 777 64494249
Dry skin 94.93 47.30 50 3656 51111 64443915
Application site inflammation 92.85 47.30 17 3689 447 64494579
Application site rash 89.03 47.30 21 3685 1933 64493093
Dermatitis 85.88 47.30 34 3672 17995 64477031
Application site reaction 73.58 47.30 15 3691 700 64494326
Skin exfoliation 72.43 47.30 40 3666 44845 64450181
Application site scab 70.92 47.30 12 3694 197 64494829
Second primary malignancy 61.31 47.30 24 3682 12313 64482713
Application site haemorrhage 54.74 47.30 13 3693 1231 64493795
Scab 53.63 47.30 20 3686 9002 64486024
Cutaneous T-cell lymphoma recurrent 53.25 47.30 8 3698 58 64494968
Lymphomatoid papulosis 52.83 47.30 10 3696 316 64494710

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 D018906 Antineoplastic Agents, Alkylating
MeSH PA D002619 Chemical Warfare Agents
MeSH PA D007509 Irritants
MeSH PA D009676 Noxae
MeSH PA D011042 Poisons
CHEBI has role CHEBI:35610 antineoplastic agents

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