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{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
{{DrugProjectFormSinglePage
! {{chembox header}}| '''Guanidine''' <!-- replace if not identical with the article name -->
|authorTag=
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Guanidine-2D-skeletal.png|150px|Skeletal formula of guanidine]] [[Image:Guanidine-3D-balls.png|150px|Ball-and-stick model of guanidine]]
|-
| [[IUPAC nomenclature|Chemical name]]
| Guanidine
|-
| [[Chemical formula]]
| CH<sub>5</sub>N<sub>3</sub>
|-
| [[Molecular mass]]
| 59.0706 g mol<sup>−1</sup>
|-
| [[CAS registry number|CAS number]]
| [113-00-8]
|-
| [[Density]]
| x.xxx g cm<sup>−3</sup>
|-
| [[Melting point]]
| 50 °C
|-
| [[Boiling point]]
| xx.x °C
|-
| [[Simplified molecular input line entry specification|SMILES]]
| C(=N)(N)N
|-
| {{chembox header}} | <small>[[wikipedia:Chemical infobox|Disclaimer and references]]</small>
|-
|}


==Overview==
'''Guanidine''' is a [[crystalline]] compound of strong [[alkalinity]] formed by the [[oxidation]] of [[guanine]]. It is used in the manufacture of [[plastics]] and [[explosives]]. It is found in [[urine]] as a normal product of protein [[metabolism]].


==Guanidinium cation==
<!--Overview-->
With a [[acid dissociation constant|p''K''<sub>a</sub>]] of 12.5, guanidine is protonated in physiological conditions, with a charge of [[Elementary charge|+1]].  This [[conjugate acid]] of guanidine is called the '''guanidinium''' [[ion|cation]], [CH<sub>6</sub>N<sub>3</sub>]<sup>+</sup>.


<gallery>
|genericName=
Image:Guanidinium-ion-3D-balls.png|<center>[[ball-and-stick model]]</center>
Image:Guanidinium-ion-2D-skeletal.png|<center>[[Resonance (chemistry)|resonance hybrid]]</center>
Image:Guanidinium-ion-canonical-forms-2D-skeletal.png|<center>canonical forms</center>
</gallery>


Notable guanidinium salts include guanidine [[hydrochloride]], which has [[chaotropic]] properties and is used to denature proteins.  Empirically, guanidine hydrochloride is known to denature proteins with a linear relationship between concentration and [[free energy]] of unfolding.


==Guanidine derivatives==
[[Image:Guanidine-group-2D-skeletal.png|thumb|right|150px|The general structure of a guanidine]]
'''Guanidines''' are a group of [[organic compound]]s sharing a common [[functional group]] with the general structure (R<sup>1</sup>R<sup>2</sup>N)(R<sup>3</sup>R<sup>4</sup>N)C=N-R<sup>5</sup>. The central bond within this group is that of an [[imine]]; the other recognizable motif within this group is an [[aminal]]. Examples of guanidines are [[triazabicyclodecene]] and [[saxitoxin]].


==Use as an alternative fuel==
|aOrAn=
Guanidine is currently being considered as an alternative fuel. In the presence of a catalyst, a mole of free-base guanidine combines with 2 moles of water to form 3 moles of ammonia and 1 mole of carbon dioxide. The ammonia can be used directly as a fuel for internal combustion engines, or decomposed into nitrogen and hydrogen gas for use in fuel cells. The guanidine could be supplied as a fuel in solid form as pure guanidine (melting point ~ 50 C) or as a lower melting point eutectic mixture with urea. Guanidine could also be supplied as solutions in ethanol, as a replacement for the gasoline component in E85 fuel.


a


|drugClass=




[[Category:amines]]
[[Category:functional groups]]
[[Category:Guanidines| ]]


[[de:Guanidin]]
|indication=
[[es:Guanadina]]
[[it:Guanidina]]
[[ja:グアニジン]]
[[pl:Guanidyna]]
[[ru:Гуанидин]]


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<!--Clinical Trials Experience-->
 
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*Anemia, leukopenia, and thrombocytopenia resulting from bone-marrow suppression attributable to guanidine have been reported. Other adverse reactions that have been observed are:
 
*General: sore throat, rash, fever.
 
*Neurologic: paresthesia of lips, face, hands, feet; cold sensations in hands and feet; nervousness, lightheadedness, jitteriness, increased irritability; tremor, trembling sensation; ataxia; emotional lability; psychotic state; confusion; mood changes, and hallucinations.
 
*Gastrointestinal: dry mouth; gastric irritation; anorexia; nausea; diarrhea; abdominal cramping. Gastrointestinal side effects may preclude the use of guanidine as a desired form of therapy.
 
*Dermatologic: rash, flushing or pink complexion; folliculitis; petechiae, purpura, ecchymoses; sweating; skin eruptions; dryness and scaling of the skin.
 
*Renal: elevation of blood creatinine, uremia; chronic interstitial nephritis, acute interstitial nephritis, and renal tubular necrosis.
 
*Hepatic: abnormal liver function tests.
 
*Cardiac: palpitation, tachycardia, atrial fibrillation, hypotension.
<!--Postmarketing Experience-->
 
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*Mild gastrointestinal disorders, such as anorexia, increased peristalsis, or diarrhea are early warnings that tolerance is being exceeded. These symptoms may be relieved by atropine, but nevertheless note should be taken of these symptoms and dosage reductions considered. Slight numbness or tingling of the lips and fingertips shortly after taking a dose of guanidine has been reported. This per se is not an indication to discontinue treatment and/or reduce dosage.
 
*Severe guanidine intoxication is characterized by nervous hyperirritability, fibrillary tremors and convulsive contractions of muscle, salivation, vomiting, diarrhea, hypoglycemia, and circulatory disturbances. Administration of intravenous calcium gluconate may control the neuromuscular and convulsive symptoms and provide some relief of other toxic manifestations.
 
*Atropine is more effective than calcium in relieving the G.I. symptoms, circulatory disturbances, and changes in blood sugar.
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*Guanidine hydrochloride tablets: 125 mg, white, round tablet; impressed with the product identification number "KEY 74" on one side. Guanidine hydrochloride tablets are available in bottles of 100 (NDC 0085-0492-01).
 
*Store at 25°C (77°F); excursions permitted to 15-30°C (59-86°F) [see USP Controlled Room Temperature].
 
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Revision as of 12:46, 22 April 2015

Guanidine
Black Box Warning
Adult Indications & Dosage
Pediatric Indications & Dosage
Contraindications
Warnings & Precautions
Adverse Reactions
Drug Interactions
Use in Specific Populations
Administration & Monitoring
Overdosage
Pharmacology
Clinical Studies
How Supplied
Images
Patient Counseling Information
Precautions with Alcohol
Brand Names
Look-Alike Names

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1];

Disclaimer

WikiDoc MAKES NO GUARANTEE OF VALIDITY. WikiDoc is not a professional health care provider, nor is it a suitable replacement for a licensed healthcare provider. WikiDoc is intended to be an educational tool, not a tool for any form of healthcare delivery. The educational content on WikiDoc drug pages is based upon the FDA package insert, National Library of Medicine content and practice guidelines / consensus statements. WikiDoc does not promote the administration of any medication or device that is not consistent with its labeling. Please read our full disclaimer here.

Black Box Warning

Title
See full prescribing information for complete Boxed Warning.
ConditionName:
  • Content

Overview

Guanidine is a that is FDA approved for the {{{indicationType}}} of . There is a Black Box Warning for this drug as shown here. Common adverse reactions include .

Adult Indications and Dosage

FDA-Labeled Indications and Dosage (Adult)

Condition1
  • Dosing Information
  • Dosage
Condition2
  • Dosing Information
  • Dosage
Condition3
  • Dosing Information
  • Dosage
Condition4
  • Dosing Information
  • Dosage

Off-Label Use and Dosage (Adult)

Guideline-Supported Use

Condition1
  • Developed by:
  • Class of Recommendation:
  • Strength of Evidence:
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Guideline-Supported Use of Guanidine in adult patients.

Non–Guideline-Supported Use

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Non–Guideline-Supported Use of Guanidine in adult patients.

Pediatric Indications and Dosage

FDA-Labeled Indications and Dosage (Pediatric)

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding FDA-Labeled Use of Guanidine in pediatric patients.

Off-Label Use and Dosage (Pediatric)

Guideline-Supported Use

Condition1
  • Developed by:
  • Class of Recommendation:
  • Strength of Evidence:
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Guideline-Supported Use of Guanidine in pediatric patients.

Non–Guideline-Supported Use

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Non–Guideline-Supported Use of Guanidine in pediatric patients.

Contraindications

  • Condition1

Warnings

Title
See full prescribing information for complete Boxed Warning.
ConditionName:
  • Content
  • Description

Precautions

  • Description

Adverse Reactions

Clinical Trials Experience

  • Anemia, leukopenia, and thrombocytopenia resulting from bone-marrow suppression attributable to guanidine have been reported. Other adverse reactions that have been observed are:
  • General: sore throat, rash, fever.
  • Neurologic: paresthesia of lips, face, hands, feet; cold sensations in hands and feet; nervousness, lightheadedness, jitteriness, increased irritability; tremor, trembling sensation; ataxia; emotional lability; psychotic state; confusion; mood changes, and hallucinations.
  • Gastrointestinal: dry mouth; gastric irritation; anorexia; nausea; diarrhea; abdominal cramping. Gastrointestinal side effects may preclude the use of guanidine as a desired form of therapy.
  • Dermatologic: rash, flushing or pink complexion; folliculitis; petechiae, purpura, ecchymoses; sweating; skin eruptions; dryness and scaling of the skin.
  • Renal: elevation of blood creatinine, uremia; chronic interstitial nephritis, acute interstitial nephritis, and renal tubular necrosis.
  • Hepatic: abnormal liver function tests.
  • Cardiac: palpitation, tachycardia, atrial fibrillation, hypotension.

Postmarketing Experience

There is limited information regarding Postmarketing Experience of Guanidine in the drug label.

Drug Interactions

  • Drug
  • Description

Use in Specific Populations

Pregnancy

Pregnancy Category (FDA):

  • Pregnancy Category


Pregnancy Category (AUS):

  • Australian Drug Evaluation Committee (ADEC) Pregnancy Category

There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of Guanidine in women who are pregnant.

Labor and Delivery

There is no FDA guidance on use of Guanidine during labor and delivery.

Nursing Mothers

There is no FDA guidance on the use of Guanidine with respect to nursing mothers.

Pediatric Use

There is no FDA guidance on the use of Guanidine with respect to pediatric patients.

Geriatic Use

There is no FDA guidance on the use of Guanidine with respect to geriatric patients.

Gender

There is no FDA guidance on the use of Guanidine with respect to specific gender populations.

Race

There is no FDA guidance on the use of Guanidine with respect to specific racial populations.

Renal Impairment

There is no FDA guidance on the use of Guanidine in patients with renal impairment.

Hepatic Impairment

There is no FDA guidance on the use of Guanidine in patients with hepatic impairment.

Females of Reproductive Potential and Males

There is no FDA guidance on the use of Guanidine in women of reproductive potentials and males.

Immunocompromised Patients

There is no FDA guidance one the use of Guanidine in patients who are immunocompromised.

Administration and Monitoring

Administration

  • Oral
  • Intravenous

Monitoring

There is limited information regarding Monitoring of Guanidine in the drug label.

  • Description

IV Compatibility

There is limited information regarding IV Compatibility of Guanidine in the drug label.

Overdosage

  • Mild gastrointestinal disorders, such as anorexia, increased peristalsis, or diarrhea are early warnings that tolerance is being exceeded. These symptoms may be relieved by atropine, but nevertheless note should be taken of these symptoms and dosage reductions considered. Slight numbness or tingling of the lips and fingertips shortly after taking a dose of guanidine has been reported. This per se is not an indication to discontinue treatment and/or reduce dosage.
  • Severe guanidine intoxication is characterized by nervous hyperirritability, fibrillary tremors and convulsive contractions of muscle, salivation, vomiting, diarrhea, hypoglycemia, and circulatory disturbances. Administration of intravenous calcium gluconate may control the neuromuscular and convulsive symptoms and provide some relief of other toxic manifestations.
  • Atropine is more effective than calcium in relieving the G.I. symptoms, circulatory disturbances, and changes in blood sugar.

Pharmacology

There is limited information regarding Guanidine Pharmacology in the drug label.

Mechanism of Action

Structure

This image is provided by the National Library of Medicine.

Pharmacodynamics

There is limited information regarding Pharmacodynamics of Guanidine in the drug label.

Pharmacokinetics

There is limited information regarding Pharmacokinetics of Guanidine in the drug label.

Nonclinical Toxicology

There is limited information regarding Nonclinical Toxicology of Guanidine in the drug label.

Clinical Studies

There is limited information regarding Clinical Studies of Guanidine in the drug label.

How Supplied

  • Guanidine hydrochloride tablets: 125 mg, white, round tablet; impressed with the product identification number "KEY 74" on one side. Guanidine hydrochloride tablets are available in bottles of 100 (NDC 0085-0492-01).
  • Store at 25°C (77°F); excursions permitted to 15-30°C (59-86°F) [see USP Controlled Room Temperature].

Storage

There is limited information regarding Guanidine Storage in the drug label.

Images

Drug Images

{{#ask: Page Name::Guanidine |?Pill Name |?Drug Name |?Pill Ingred |?Pill Imprint |?Pill Dosage |?Pill Color |?Pill Shape |?Pill Size (mm) |?Pill Scoring |?NDC |?Drug Author |format=template |template=DrugPageImages |mainlabel=- |sort=Pill Name }}

Package and Label Display Panel

{{#ask: Label Page::Guanidine |?Label Name |format=template |template=DrugLabelImages |mainlabel=- |sort=Label Page }}

Patient Counseling Information

There is limited information regarding Patient Counseling Information of Guanidine in the drug label.

Precautions with Alcohol

  • Alcohol-Guanidine interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.

Brand Names

Look-Alike Drug Names

Drug Shortage Status

Price

References

The contents of this FDA label are provided by the National Library of Medicine.

  1. ↑ Empty citation (help)
  2. ↑ "http://www.ismp.org". External link in |title= (help)


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