CHEM 320A:

Application of Organic
Chemistry
INSTRUCTOR
Urbano
SCHEDULE
AM-830 AM)
ROOM
PRESENTOR

: Mme. Erced E.
: MTThF (730
: 240
1
: Ryan B. Laytani,

INTRODUCTION

ARTICLE:
Treatment of ethylene
glycol and methanol
poisoning: why ethanol?
AUTHORS:
MGG Sturkenboom, HM
van Rieke, and DRA
Uges
SOURCE:
Netherlands Journal of
Critical Care (2009)
2

REASON FOR CHOOSING THE

TOPIC

GMA 7 documentary

An OFW drank a locally produced

alcoholic liquor contaminated
with methanol
Lost his vision hours after
drinking
Did not communicate to his
family because of depression and
fear of rejection
Returned to his family after two
years of isolation as
PERMANENTLY BLIND MAN

I
I want
want to
to know
know the
the immediate
immediate
treatment
treatment for
for alcohol/methanol
alcohol/methanol
poisoning
poisoning so
so that
that this
this
situation
situation will
will not
not happen
happen
to
to me,
me, to
to my
my family,
family, or
or to
to other
other3people.
people.

BACKGROUND

Ethanol
Used

as antidote for
alcohol poisoning since
1940s

Fomepizole
Recommended

more
often than ethanol as
poison antidote by
several research authors
Several of these authors
are connected with
pharmaceutical industries
4

OBJECTIVES
This research article aims
to:
1. Describe ethylene glycol
and methanol poisoning
2. Compare ethanol and
fomepizole as an antidote
for ethylene glycol and
methanol poisoning
3. Recommend the more
effective antidote
5

ETHYLENE GLYCOL

Used as unauthorized
wine sweetener
Present in antifreeze
to prevent pipe
bursting and
coolants
Metabolized more
rapidly than methanol
Lethal dose: 1.4
mL/kg bodyweight

IUPAC:
IUPAC: 1,21,2ETHANEDIOL
ETHANEDIOL

ETHYLENE GLYCOL POISONING

Metabolism Process
Alcohol dehydrogenase enzyme that oxidizes ethylene
glycol
20% of ethylene glycol is
excreted unchanged by the
kidneys

Glycolic and oxalic acid are

responsible for metabolic
acidosis and renal damages
Oxalic acid binds to calcium
forming insoluble calcium
oxalate crystals causing acute
renal failure, neurological,
and pulmonary dysfunction

ETHYLENE
ETHYLENE
GLYCOL
GLYCOL
URINAR
URINAR
YY
EXCRETI
EXCRETI
ON
ON
GLYCOALDEHYDE
GLYCOALDEHYDE

GLYCOLIC
GLYCOLIC ACID
ACID

OXALIC
OXALIC ACID
ACID
7

CHEMICAL REACTIONS OF ETHYLENE

GLYCOL

METHANOL

Used as a solvent for

cleaning solutions, dyes,
adhesives, thinners, and
paint removers
Cheap substitute of
ethanol
Methanol itself causes
little toxicity
Metabolized into toxic
metabolites in the liver
Lethal dose: 1-2 mL/kg

STRUCTURAL
STRUCTURAL
FORMULA
FORMULA

METHANOL POISONING

Metabolism Process
Alcohol

dehydrogenase
(ADH) - enzyme that oxidizes
methanol into formaldehyde
Aldehyde dehydrogenase
enzyme that rapidly converts
formaldehyde into formic
acid

Formic Acid is responsible

for the metabolic acidosis,
visual disturbances,
permanent blindness, and
mortality

METHANOL
METHANOL

FORMALDEHYDE
FORMALDEHYDE

FORMIC
FORMIC ACID
ACID
10

CHEMICAL REACTIONS OF
METHANOL

11

ETHANOL AS AN ANTIDOTE

Used as an antidote for

many decades but never
been registered by
pharmaceutical industry
Higher affinity to alcohol
dehydrogenase compared
to methanol and ethylene
glycol
Can be administered orally
or intravenously
Any kind of commercially
available ethanol can be
used for oral administration

CHEMICAL
CHEMICAL
REACTIONS
REACTIONS

12

ETHANOL DOSE
RECOMMENDATIONS

Intravenous Administration

Can be infused as 10% solution in 5% dextrose

100 mL of 96% (v/v) ethanol contains 77 g of
ethanol

Loading Dose

600 1,000 mg/kg body weight depending on the

blood level of ethanol

Maintenance Dose
Needed to maintain target ethanol concentration
(1,000 to 1,500 mg/L)
Enough to saturate ADH thus inhibiting further
toxic alcohol metabolism

13

FOMEPIZOLE AS AN ANTIDOTE

Competitive inhibitor of
ADH
Affinity to ADH is
approximately 500 to 8,000
times higher than ethanol
Registered antidote for
methanol and ethylene
glycol poisoning
Efficacy is derived from
case studies and two
prospective clinical trials
Can be administered orally
but is only registered as an
intravenous preparation

STRUCTURAL
STRUCTURAL
FORMULA
FORMULA

14

FOMEPIZOLE DOSE
RECOMMENDATIONS

Loading Dose

Maintenance Dose

15 mg/kg body weight

10 15 mg/kg bodyweight per 12 hours

Several children treated with

fomepizole after a loading dose of
ethanol
Not officially approved for use in
children
15

SUMMARY OF DOSE
RECOMMENDATIONS

16

HAEMODIALYSIS

Removes waste
products from blood
when kidneys are in a
state of renal failure
Corrects metabolic
imbalance
Only method for
removal of ethylene
glycol if renal failure is
present
Should be undertaken
for both methanol and
ethylene glycol
poisoning 17

TREATMENT COST IN 2009

Ethanol treatment:
Intravenous treatment with 96% sterile
ethanol for 60 hours is approximately PhP
2,000
Fomipazole treatment:
One vial (100 mg/20 mL) costs PhP 6,000
Loading dose of 15 mg/kg costs
approximately PhP 66,000
If five doses (treatment for 48 hours), the
treatment will amount to roughly PhP
258,000
Additional costs for hemodialysis, etc.
18

COMPARISON OF
ETHANOL AND FOMIPAZOLE
TREATMENT
ADVANTAGES

ETHANOL
1.
2.
3.
4.

Available in clinical
setting
Antidote in different
alcohol poisonings
Administered orally and
intravenously
Extensive experience in
Netherlands

FOMEPIZOLE
1.
2.

Minimal adverse effects

Registered for ethylene
glycol poisoning

19

COMPARISON OF
ETHANOL AND FOMIPAZOLE
TREATMENT
DISADVANTAGES
ETHANOL
1.
2.

3.

Dose calculations based

on blood alcohol levels
Hospitalization in ICU
necessary during
treatment
Not officially registered as
antidote

FOMEPIZOLE
1.
2.
3.
4.
5.
6.

High costs
Not available in clinical
settings
Limited shelf life
Not applied for other alcohol
poisonings
Lack of experience in
Netherlands
Not registered for methanol
poisoning in Netherlands
20

CONCLUSION
1.

2.

3.

Ethanol is still the

antidote of choice for
ethylene glycol and
methanol poisoning
Minimal adverse
effects of fomepizole
do not justify its high
treatment cost
Ethanol can treat
toxic alcohol
poisonings safely
and effectively
21

REFERENCES
1.

2.

Sturkenboom, M., van Rieke, H. & Uges, D.

Treatment of ethylene glycol and methanol
poisoning: why ethanol? Netherlands Journal
of Critical Care 2009, 13, 297-302.
Wikipedia the free online encyclopedia.
(Retrieved on July 31, 2014). Available Online:
http://en.wikipedia.org/wiki/.
Keywords:
Antidote, ethanol, ethylene glycol, fomepizole
haemodialysis, and methanol

22

CHIKOYS STRUGGLE ON
It was a coldCARBOXYLIC
rainy morning and ACID
Chikoy woke up at
7:20 AM with a slight headache. He had an
exam at 7:30 AM. He did not take a bath
because its already late. He washed his face
with soap but it will not make bubbles and a
stick mass congealed in his face.
Chikoy decided to eat a breakfast consisting of
milk and bread with butter. When he opened
the refrigerator, he smelled a variety of sour
odors like the rancid butter and decomposing
milk. He forgot that there was a power outage
the previous day and all through the night.
23

continuation of CHIKOYS
Chikoy just eatSTRUGGLE
some leftover rice, dried

fish
dipped with vinegar, and orange for breakfast.
He also opened the medicine box and looked
for aspirin tablet for his headache but he
cannot find one.
On the way to CIT-U, Chikoy had to run through
the muddy road near his home. Unfortunately,
he slipped and landed on an ant hill. These
ants were biting his arms and neck.
Chikoy arrived at his class twenty minutes late
with dirty clothes, itchy body parts, and sweaty
face.
24

Continuation of CHIKOYS
STRUGGLE
Fortunately, THE BIG GUY above was watching
over the struggles of Chikoy for he was just on
time to receive the examination questionnaire.
One silver lining in Chikoys gloomy morning was
that

25

Continuation CHIKOYS
STRUGGLE
.. his teacher was also LATE!!!
THANK
YOU!!!

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