Mitoguazone

Modify Date: 2026-07-03 20:50:05

Mitoguazone Structure
Mitoguazone structure
Common Name Mitoguazone
CAS Number 459-86-9 Molecular Weight 184.20200
Density 1.55g/cm3 Boiling Point 436.6ºC at 760mmHg
Molecular Formula C5H12N8 Melting Point N/A
MSDS N/A Flash Point 217.8ºC

 Use of Mitoguazone


Mitoguazone (Methylglyoxal-bis(guanylhydrazone)) is a synthetic polycarbonyl derivative with potent antineoplastic activity. Mitoguazone is a brain-penetrant and competitive S-adenosyl-methionine decarboxylase (SAMDC) inhibitor that disrupts polyamine biosynthesis. Mitoguazone induces cell apoptosis. Mitoguazone inhibits HIV DNA integration into the cellular DNA in both monocytes and macrophages. Mitoguazone has the potential for acute leukemia, Hodgkin's and non-Hodgkin's lymphoma treatment[1][2][3][4].

 Names

This table lists Chinese names, IUPAC names and various aliases of this chemical substance.

Name mitoguazone
Synonym More Synonyms

 Mitoguazone Biological Activity

This table contains bioactivity, target information and biological‑assay experimental data of this compound.

Description Mitoguazone (Methylglyoxal-bis(guanylhydrazone)) is a synthetic polycarbonyl derivative with potent antineoplastic activity. Mitoguazone is a brain-penetrant and competitive S-adenosyl-methionine decarboxylase (SAMDC) inhibitor that disrupts polyamine biosynthesis. Mitoguazone induces cell apoptosis. Mitoguazone inhibits HIV DNA integration into the cellular DNA in both monocytes and macrophages. Mitoguazone has the potential for acute leukemia, Hodgkin's and non-Hodgkin's lymphoma treatment[1][2][3][4].
Related Catalog
In Vitro Mitoguazone competitively inhibits spermidine synthesis in lymphocytes at concentrations as low as 0.5 μg/mL. Levels of 30 μg/mL or more inhibit protein synthesis and mitochondrial respiration[1]. The ability of Mitoguazone to induce apoptosis by inhibiting the polyamine pathway is assessed in three Burkitt's lymphoma cell lines (Raji, Ramos and Daudi) and one prostate carcinoma cell line (MPC 3). Mitoguazone induces apoptosis in all the different human cancer cell lines tested in a concentration- and time-dependent way, and triggers a p53-independent programmed cell death in the human breast cancer MCF7 cell line[2].
In Vivo The influence of different stages of leukemia P388 on the pharmacokinetics of the antineoplastic agent Mitoguazone in mice is investigated. Independent of the tumor stage investigated, the total clearance of mitoguazone is slightly reduced reflecting a moderate increase of AUC in the serum of leukemia-bearing animals. Furthermore, in an advanced tumor stage the drug levels in kidneys, liver, spleen and serum are found to be elevated to some extent in comparison to tumor-free controls in contrast to an earlier stage of leukemia[5].
References

[1]. J Rizzo, et al. Pharmacokinetic Profile of Mitoguazone (MGBG) in Patients With AIDS Related non-Hodgkin's Lymphoma. Invest New Drugs. 1996;14(2):227-34.

[2]. K Davidson, et al. Mitoguazone Induces Apoptosis via a p53-independent Mechanism. Anticancer Drugs. 1998 Aug;9(7):635-40.

[3]. Xia Jin, et al. Inhibition of HIV Expression and Integration in Macrophages by Methylglyoxal-Bis-Guanylhydrazone. J Virol. 2015 Nov;89(22):11176-89.

[4]. A M Levine, et al. Mitoguazone Therapy in Patients With Refractory or Relapsed AIDS-related Lymphoma: Results From a Multicenter Phase II Trial. J Clin Oncol. 1997 Mar;15(3):1094-103.

[5]. R Amlacher, et al. Influence of Leukemia P388 on the Pharmacokinetics of Mitoguazone in B6D2F1 Mice. Pharmazie. 1990 May;45(5):364-6.

 Chemical & Physical Properties

This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.

Density 1.55g/cm3
Boiling Point 436.6ºC at 760mmHg
Molecular Formula C5H12N8
Molecular Weight 184.20200
Flash Point 217.8ºC
Exact Mass 184.11800
PSA 148.52000
LogP 0.69610
Vapour Pressure 7.99E-08mmHg at 25°C
Index of Refraction 1.692
InChIKey MXWHMTNPTTVWDM-NXOFHUPFSA-N
SMILES CC(C=NN=C(N)N)=NN=C(N)N

 Toxicological Information

This table summarizes toxicological test data, acute & chronic toxicity and ecological hazard parameters for this chemical.

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MF3860000
CHEMICAL NAME :
Guanidine, 1,1'-((methylethanediylidene)dinitrilo)di-
CAS REGISTRY NUMBER :
459-86-9
LAST UPDATED :
199612
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C5-H12-N8
MOLECULAR WEIGHT :
184.25

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1260 mg/kg
SEX/DURATION :
male 7 day(s) pre-mating female 7 day(s) pre-mating - 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Mammal - cattle Lymphocyte
DOSE/DURATION :
8 umol/L
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 37,3169,1977

 MitoguazoneBioassay

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This table contains target information, in‑vitro & in‑vivo assay data for this compound.

Name: Antitumor activity against leukemia cell lines of the NCI60 panel
Source: ChEMBL
Target: NON-PROTEIN TARGET
External Id: CHEMBL909878
Name: Antitumor activity against NSCLC cell lines of the NCI60 panel
Source: ChEMBL
Target: NSCLC
External Id: CHEMBL909879
Name: Antitumor activity against renal cell lines of the NCI60 panel
Source: ChEMBL
Target: NON-PROTEIN TARGET
External Id: CHEMBL909884
Name: Antitumor activity against prostate cell lines of the NCI60 panel
Source: ChEMBL
Target: NON-PROTEIN TARGET
External Id: CHEMBL909885
Name: Antitumor activity against breast cell lines of the NCI60 panel
Source: ChEMBL
Target: NON-PROTEIN TARGET
External Id: CHEMBL909886
Name: Antitumor activity against colon cell lines of the NCI60 panel
Source: ChEMBL
Target: NON-PROTEIN TARGET
External Id: CHEMBL909880
Name: Antitumor activity against CNS cell lines of the NCI60 panel
Source: ChEMBL
Target: NON-PROTEIN TARGET
External Id: CHEMBL909881
Name: Antitumor activity against melanoma cell lines of the NCI60 panel
Source: ChEMBL
Target: NON-PROTEIN TARGET
External Id: CHEMBL909882
Name: Antitumor activity against ovarian cell lines of the NCI60 panel
Source: ChEMBL
Target: NON-PROTEIN TARGET
External Id: CHEMBL909883
Name: Choleostatic liver toxicity, either proven histopathologically or where the ratio of ...
Source: ChEMBL
Target: N/A
External Id: CHEMBL3137727
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 Synonyms

This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.

Mitoguazone
Me-GAG
Pyruvaldehyde bis(amidinohydrazone)
2,2'-(1-Methyl-1,2-ethanediylidene)bis(hydrazinecarbimidamide)
methylglyoxal bis-(guanylhydrazone)
1,1'-((methylethanediylidene)dinitrilo)diguanidine
2,2'-(1-methyl-1,2-ethanediylidene)bis-hydrazinecarboximidamid
methyl-g
MGBG
methyl-gag
1,1'-((methylethanediylidene)dinitrilo)di-guanidin

 Mitoguazone | FAQ

This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.

Q: What is the polar surface area (PSA) of mitoguazone?
A: Polar surface area (PSA) of mitoguazone is 148.52000.
Q: What is the SMILES notation of mitoguazone?
A: SMILES notation of mitoguazone is CC(C=NN=C(N)N)=NN=C(N)N.
Q: What English synonyms does mitoguazone have?
A: English synonyms of mitoguazone: Mitoguazone, Me-GAG, Pyruvaldehyde bis(amidinohydrazone), 2,2'-(1-Methyl-1,2-ethanediylidene)bis(hydrazinecarbimidamide), methylglyoxal bis-(guanylhydrazone), 1,1'-((methylethanediylidene)dinitrilo)diguanidine, 2,2'-(1-methyl-1,2-ethanediylidene)bis-hydrazinecarboximidamid, methyl-g, MGBG, methyl-gag, 1,1'-((methylethanediylidene)dinitrilo)di-guanidin.
Q: What is the molecular weight of mitoguazone?
A: Molecular weight of mitoguazone is 184.20200.
Q: What is the English name of mitoguazone?
A: The English name of mitoguazone is mitoguazone.
Q: What is the boiling point of mitoguazone?
A: Boiling point of mitoguazone is 436.6ºC at 760mmHg.
Q: What is the molecular formula of mitoguazone?
A: Molecular formula of mitoguazone is C5H12N8.
Q: What is the LogP of mitoguazone?
A: LogP of mitoguazone is 0.69610.
Q: What is the InChIKey of mitoguazone?
A: InChIKey of mitoguazone is MXWHMTNPTTVWDM-NXOFHUPFSA-N.
Q: What is the CAS number of mitoguazone?
A: CAS number of mitoguazone is 459-86-9.

 Mitoguazonefactory

This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.

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