mechlorethamine 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 531.47 54.24 79 633 807 2356566
Application site pain 402.70 54.24 67 645 1459 2355914
Application site erythema 385.66 54.24 63 649 1217 2356156
Pruritus 322.97 54.24 103 609 43237 2314136
Application site discolouration 256.88 54.24 36 676 224 2357149
Skin discolouration 233.04 54.24 52 660 5368 2352005
Erythema 220.08 54.24 68 644 25091 2332282
Application site irritation 212.17 54.24 33 679 449 2356924
Skin irritation 190.23 54.24 35 677 1350 2356023
Therapy non-responder 181.93 54.24 46 666 8058 2349315
Application site vesicles 135.18 54.24 22 690 402 2356971
Skin burning sensation 124.48 54.24 26 686 1930 2355443
Application site dryness 102.61 54.24 14 698 68 2357305
Blister 101.59 54.24 28 684 6743 2350630
Disease progression 91.20 54.24 32 680 17063 2340310
Skin hyperpigmentation 87.05 54.24 17 695 893 2356480
Application site discharge 86.38 54.24 12 700 68 2357305
Dry skin 74.86 54.24 22 690 6630 2350743
Application site exfoliation 72.30 54.24 11 701 126 2357247
Rash 71.90 54.24 39 673 59519 2297854
Cutaneous T-cell lymphoma 62.91 54.24 11 701 311 2357062
Application site rash 61.85 54.24 12 700 607 2356766
Application site inflammation 60.08 54.24 9 703 92 2357281
Skin lesion 57.29 54.24 16 696 4009 2353364
Application site warmth 55.62 54.24 8 704 60 2357313
Large intestine polyp 54.99 54.24 12 700 1086 2356287
Skin disorder 54.27 54.24 15 697 3616 2353757

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 555.45 77.04 79 752 257 1745693
Application site erythema 490.45 77.04 77 754 557 1745393
Application site pain 400.82 77.04 66 765 660 1745290
Pruritus 368.91 77.04 115 716 23107 1722843
Skin irritation 245.63 77.04 44 787 736 1745214
Therapy non-responder 229.53 77.04 60 771 6206 1739744
Erythema 218.11 77.04 69 762 14119 1731831
Application site irritation 217.62 77.04 33 798 178 1745772
Application site vesicles 197.13 77.04 30 801 166 1745784
Skin burning sensation 155.59 77.04 30 801 754 1745196
Blister 138.92 77.04 37 794 4055 1741895
Application site discolouration 136.45 77.04 20 811 81 1745869
Disease progression 132.09 77.04 50 781 17213 1728737
Skin discolouration 131.39 77.04 33 798 2863 1743087
Cutaneous T-cell lymphoma 118.71 77.04 21 810 321 1745629
Application site discharge 110.78 77.04 15 816 28 1745922
Dry skin 104.54 77.04 29 802 3683 1742267
Application site burn 90.33 77.04 14 817 88 1745862
Skin exfoliation 85.73 77.04 26 805 4509 1741441
Second primary malignancy 84.07 77.04 19 812 1040 1744910

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

Drug Use (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

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 0.016% BASE VALCHLOR HELSINN N202317 Aug. 23, 2013 RX GEL TOPICAL Aug. 23, 2020 TOPICAL TREATMENT OF STAGE 1A AND 1B MYCOSIS FUNGOIDES-TYPE CUTANEOUS T-CELL LYMPHOMA IN PATIENTS WHO HAVE RECEIVED PRIOR SKIN-DIRECTED THERAPY

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
DNA DNA OTHER CHEMBL CHEMBL

External reference:

IDSource
4019808 VUID
N0000147897 NUI
C0025033 UMLSCUI
D04872 KEGG_DRUG
50D9XSG0VR UNII
586 INN_ID
372692002 SNOMEDCT_US
29156002 SNOMEDCT_US
4019808 VANDF
6674 RXNORM
d01339 MMSL
387071000 SNOMEDCT_US
29634 MMSL
004816 NDDF
4033 PUBCHEM_CID
CHEBI:28925 CHEBI
CHEMBL427 ChEMBL_ID
DB00888 DRUGBANK_ID
55-86-7 SECONDARY_CAS_RN
CHEMBL1201001 ChEMBL_ID
D008466 MESH_DESCRIPTOR_UI
7218 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
VALCHLOR HUMAN PRESCRIPTION DRUG LABEL 1 66215-016 GEL 0.01 g TOPICAL NDA 17 sections
VALCHLOR HUMAN PRESCRIPTION DRUG LABEL 1 69639-120 GEL 0.01 g TOPICAL NDA 17 sections