56-03-1 Usage
Description
Biguanide is a class of oral antidiabetic drugs that promote euglycemia (antihyperglycemic) and are used for the management of mild to moderately severe noninsulin-dependent diabetes mellitus (NIDDM or Type II) in obese or overweight patients, typically above 40 years of age. Metformin, a well-known Biguanide, was first introduced as a treatment for diabetes in 1957 and has become the most widely prescribed antidiabetic drug worldwide. Biguanides are not hypoglycemic agents but help control hyperglycemia, and they can be used as monotherapy or in combination with other oral hypoglycemic agents. However, they have been associated with a risk of lactic acidosis, which led to the withdrawal of phenformin from the US market in 1976.
Uses
1. Used in Pharmaceutical Industry:
Biguanide is used as an oral drug for the management of mild to moderately severe noninsulin-dependent diabetes mellitus (NIDDM or Type II) in obese or overweight patients, usually above 40 years of age, with adult-onset disease.
2. Used in Water Treatment Industry:
Polymeric biguanides were originally developed as a presurgery antimicrobial scrub and later introduced in 1977 for treating pools and spas as a disinfectant under the trade name Baquacil. The US Environmental Protection Agency approved this agent as the only nonhalogen sanitizer for pools and spas. Biguanides are used in combination with algaecides and hydrogen peroxide for periodic oxidation of pools and spas.
3. Used in Disinfection and Preservation:
Biguanide in the form of polyaminopropyl biguanide serves as a disinfectant and preservative for various applications, including skin disinfection, contact lens cleaning solutions, and deodorant body sprays. Biguanides reduce the surface tension of water, providing a smoother feeling, and are stable in sunlight and temperature. At recommended concentrations, they do not irritate the skin or eyes and do not corrode pool equipment.
4. Used in Compatibility with Water Treatment Chemicals:
Biguanides are compatible with water ion balancing chemicals, making them suitable for use in water treatment processes where such chemicals are employed. They are, however, incompatible with chlorine, ozone, detergents, and ionizers.
Environmental Fate
Globally, hundreds of millions of patients are prescribed this
drug annually. Metformin was discovered before the era of
target-based drug discovery, and its molecular mechanism of
action remains an important focus of diabetes research.
Advances in our understanding of metformin’s molecular
targets are likely to enable target-based identification of secondgeneration
drugs with similar properties, a development that
has been a difficult task until now. Besides its potent antidiabetic
properties, Metformin’s potential as a targeted anticancer
agent is being explored in a number of laboratories throughout
the world.
Purification Methods
Crystallise biguanide from EtOH. It gives a red Cu derivative, and it forms salts with many metals. The monohydrochloride has m 235o [38664-03-8] and the dihydrochloride forms plates with m 248o (213-214o, also reported) [25836-74-2]. [Beilstein 3 H 93, 3 I 44, 3 II 76, 3 III 171, 3 IV 162.]
Toxicity evaluation
Biguanides, salts of biguanide, or biguanide-like compounds
such as Metformin hydrochloride production and use as an
antidiabetic medication may result in its release to the
environment through various waste streams. Metformin
hydrochloride is expected to exist in the dissociated form as
metformin in the environment. If released to air, an estimated
vapor pressure of 0.0034 mm Hg at 25 °C indicates
metformin will exist solely in the vapor phase in the
ambient atmosphere. Metformin, when in vapor phase, is
expected to be degraded in the atmosphere by reaction with
photochemically-produced hydroxyl radicals; the half-life for
this reaction in air is estimated to be 15 min. If released to
soil, metformin is expected to have high mobility based on
an estimated Koc of 110. Volatilization from moist soil
surfaces is not expected to be an important fate process
based on an estimated Henry’s law constant of
7.6×10-16 atm-cu m mol-1. The pKa of metformin is 12.4,
indicating that this compound will primarily exist in cation
form in the environment, and cations generally adsorb to
organic carbon and clay more strongly than their neutral
counterparts. Based on metformin’s vapor pressure, it is not
expected to volatilize from dry soil surfaces. Based on the
estimated Koc of metformin, it is not expected to adsorb to
suspended solids and sediment if released into water. Volatilization
from water surfaces is not expected to be an
important fate process based on this compound’s estimated
Henry’s law constant. Furthermore, a pKa of 12.4 indicates
metformin will exist almost entirely in the ionized form at
pH values of 5–9. An estimated bioconcentration factor of
3.2 suggests the potential for bioconcentration in aquatic
organisms is low. Hydrolysis is not expected to be an
important environmental fate process since this compound
lacks functional groups that hydrolyze under environmental
conditions. Occupational exposure to metformin hydrochloride
may occur through inhalation and dermal contact
with this compound at workplaces where metformin
hydrochloride is produced or used.
Check Digit Verification of cas no
The CAS Registry Mumber 56-03-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 6 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 56-03:
(4*5)+(3*6)+(2*0)+(1*3)=41
41 % 10 = 1
So 56-03-1 is a valid CAS Registry Number.
InChI:InChI=1/C2H7N5/c3-1(4)7-2(5)6/h(H7,3,4,5,6,7)
56-03-1Relevant articles and documents
Regioselective synthesis of pyrimido[1,2-a][1,3,5]triazin-6-ones via reaction of 1-(6-oxo-1,6-dihydropyrimidin-2-yl)guanidines with triethylorthoacetate: Observation of an unexpected rearrangement
Sachdeva, Nikhil,Dolzhenko, Anton V.,Keung Chui, Wai
scheme or table, p. 4586 - 4596 (2012/07/28)
A novel thermal rearrangement, involving pyrimidine ring opening and subsequent ring closure leading to recyclization of the system, was identified in the reaction of (6-oxo-1,6-dihydropyrimidin-2-yl)guanidines 3 (where NR 1R2 = NH2, NH alkyl, NH aralkyl, NHCH 2Ph(R)) with triethyl orthoacetate, affording 4-substituted-2-methyl- 6H-pyrimido[1,2-a][1,3,5]triazin-6-ones 6 and their ring opened products. However, no such rearrangement was observed with (6-oxo-1,6-dihydropyrimidin-2- yl)guanidines 3 bearing a tertiary amino or anilino substituent (i.e. where NR1R2 = N(CH3)2, indoline, morpholino, NHAr). As expected, 2-substituted-4-methyl-6H-pyrimido[1,2-a][1,3,5] triazin-6-ones 4 were obtained as the final products. Experimental structural determination and theoretical studies were carried out to get an understanding of the observed thermal rearrangement. In addition, an attempt to obtain similar pyrimido[1,2-a][1,3,5]triazin-6-ones using N,N-dimethylacetamide dimethyl acetal (DMA-DMA) as one carbon inserting synthon had furnished triazine ring annulated product 14 bearing N,N-dimethyl enamino substituent at position 4 as a result of further reaction with a second molecule of DMA-DMA.
3-deoxyglucosone and skin
-
, (2008/06/13)
The invention relates to a method of removing 3-deoxyglucosone and other alpha-dicarbonyl sugars from skin. The invention further relates to methods of inhibiting production and function of 3-deoxyglucosone and other alpha-dicarbonyl sugars in skin. The invention also relates to methods of treating 3-deoxyglucosone and other alpha-dicarbonyl sugars associated diseases and disorders of skin.
Biguanides and derivatives thereof as inhibitors of advanced glycosylation of a target protein
-
, (2008/06/13)
The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises an agent capable of inhibiting the formation of advanced glycosylation endproducts of target proteins by reacting with the carbonyl moiety of the early glycosylation product of such target proteins formed by their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.